Hydrochloric Acid → (4aR,4bS,6aS,7S,9aS,9bS,11aR)-4a,6a-dimethyl-2-oxohexadecahydro-1H-indeno[5,4-f]quinoline-7-carboxylic acid

HRID 253715Notes

Reaction equation

HRID 253715 reaction equation
[CH3:1][C@@:2]12[C@@H:10]([C:11](NC(C)(C)C)=[O:12])[CH2:9][CH2:8][C@H:7]1[C@@H:6]1[CH2:18][CH2:19][C@H:20]3[NH:26][C:24](=[O:25])[CH2:23][CH2:22][C@:21]3([CH3:27])[C@H:5]1[CH2:4][CH2:3]2.Cl.C[OH:30]>>[CH3:1][C@@:2]12[C@@H:10]([C:11]([OH:30])=[O:12])[CH2:9][CH2:8][C@H:7]1[C@@H:6]1[CH2:18][CH2:19][C@H:20]3[NH:26][C:24](=[O:25])[CH2:23][CH2:22][C@:21]3([CH3:27])[C@H:5]1[CH2:4][CH2:3]2

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 9864387(4aR,4bS,6aS,7S,9aS,9bS,11aR)-N-(tert-butyl)-4a,6a-dimethyl-2-oxohexadecahydro-1H-indeno(5,4-f)quinoline-7-carboxamide

Product 1

HCID 9818495(4aR,4bS,6aS,7S,9aS,9bS,11aR)-4a,6a-dimethyl-2-oxohexadecahydro-1H-indeno[5,4-f]quinoline-7-carboxylic acid

Procedure

A suspension of 100 g (0.26 mol) of dihydrofinasteride, 480 g of 20% HCl solution (2.63 mol) and 120 g of methanol are heated to reflux and boiled intensively for 8-12 hours. The reactant goes into solution on heating; after 8 hours, there is a suspension which can be readily filtered. The filtercake is washed three times intensively with 100 g each time of water, suction-dried for approx. 15 minutes and subsequently dried overnight. Yield: 60 g.

Workup

  1. temperatureare heated
  2. temperatureto reflux
  3. temperatureon heating
  4. waitafter 8 hours
  5. filtrationcan be readily filtered
  6. washThe filtercake is washed three times intensively with 100 g each time of water
  7. customsuction-dried for approx. 15 minutes and subsequently dried overnight

Sources & evidence

ORD record
ord-fcb6df2dbd7a4c38baa5665ba1edc0c3
Source dataset
uspto-grants-2011_01
Patent number
US07872135B2

Reaction notes

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