Process for the manufacturing of (6aR,10aR)-7-propyl-6,6a,7,8,9,10,10a,11-octahydro-[1,3]dioxolo[4′,5′:5,6]benzo[1,2-G]quinoline and (4aR,10aR)-1-propyl-1,2,3,4,4a,5,10,10a-octahydro-benzo[G]quinoline-6,7-diol

1. A process for the manufacture of compound (I) with the formula below

from the compound (Ib) with the formula below

wherein compound (Ib) is prepared by a process comprising the steps of:

Step 0)

Substep (i) reacting compound (A1) with 3-chloropropan-1-amine to obtain compound (a2i); or

Substep (S1) reacting compound (a6i) with tert-butyl 2-bromoacetate and zinc to form a mixture, followed by

treating the mixture from substep (S1) with acetic acid, followed by

reacting said mixture with 3-chloropropan-1-amine hydrochloride to afford compound (a2i);

followed by

Step 1)

Substep (ii) reducing the compound (a2i) obtained in substep (i) or substep (S1) to obtain compound (a2ii), followed by

Substep (iii) resolving compound (a2ii) using L-tartaric acid to afford compound (A2-hemi-L-tartrate);

or

Substep (i) or substep (S1) is followed by substep (iv) comprising the step of subjecting compound (a2i) to a hydrogenation performed with a chiral catalyst in the presence of hydrogen and a solvent to afford compound (A2);

according to the reaction scheme below:

2. The process according to claim 1 , wherein compound (Ib) is prepared by a process comprising the steps of:

Step 0)

Substep (S1)

reacting compound (a6i) with tert-butyl 2-bromoacetate and zinc to form a mixture, followed by

treating the mixture from substep (S1) with acetic acid, followed by

reacting said mixture with 3-chloropropan-1-amine hydrochloride to afford compound (a2i);

followed by

Step 1)

Substep (ii) reducing the compound (a2i) obtained in substep (S1) to obtain compound (a2ii), followed by

Substep (iii) resolving compound (a2ii) using L-tartaric acid to afford compound (A2-hemi-L-tartrate).

3. The process according to claim 1 , wherein the chiral catalyst in Step 1 substep (iv) is selected from (2S)-1-[(1S)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-(diphenylphosphino)ferrocene and bis(2,5-norbornadiene)rhodium(I) tetrafluoroborate.

4. The process according to claim 1 , wherein the solvent in Step 1 substep (iv) is 2,2,2-trifluoroethanol.

5. The process according to claim 1 , wherein the reduction in Step 1 substep (ii) takes place in the presence of a reducing agent selected from the group consisting of NaBH 3 CN, sodium triacetoxyborohydride (STAB), a borane, 5-ethyl-2-methylpyridine borane (PEMB) and NaBH 4 .

6. The process according to claim 1 , wherein the reduction in Step 1 substep (ii) takes place by use of a platinum catalyst.

7. A process for the manufacture of compound (I):

from compound (Ib):

wherein compound (Ib) is prepared by a process comprising the following step

2) reacting compound (A2) or compound (A2-hemi-L-tartrate) with propanal in the presence of a reducing agent,

to afford compound (A3) according to reaction scheme a) or b) below

8. A process for the manufacture of compound (I):

from compound (Ib):

wherein compound (Ib) is prepared by a process comprising the following step

3) reacting compound (A3) with a strong base, to afford compound A4 according to the reaction scheme below

optionally followed by isolating compound (A4), or a salt thereof.

9. The process according to claim 8 , wherein A4 is isolated as a HCl salt as depicted below

10. A process for the manufacture of compound (I):

from compound (Ib):

wherein compound (Ib) is prepared by a process comprising the following step

4) performing an intramolecular Friedel-Craft acylation of compound (A4) to afford compound (A5) according to the reaction scheme below:

optionally followed by isolating compound (A5), or a salt thereof.

11. A process for the manufacture of compound (I):

from compound (Ib):

wherein compound (Ib) is prepared by a process comprising the following step

5) reducing compound (A5), or a salt thereof, to obtain compound (Ib), or a salt thereof according to the reaction scheme below

12. The process according to claim 11 , wherein compound (I) is prepared from compound (Ib) by the following step

6) reacting compound (Ib) with a Lewis acid or Brønsted acid selected from the group consisting of BCl 3 , BBr 3 and HBr,

to obtain compound (I) according to the reaction scheme below

13. The process according to claim 6 , wherein the platinum catalyst is platinum on carbon.