Citric Acid → 5-((5aR,6S)-1-(4-fluorophenyl)-5a-methyl-5,5a,6,7,8,9-hexahydroimidazo[1,5-b]isoquinoline-6-carbonyl)thiophene-2-carboxylic acid

HRID 1876917Notes

Reaction equation

HRID 1876917 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[CH:10][N:11]3[C:20]=2[CH:19]=[C:18]2[C@@:13]([CH3:32])([C@@H:14]([C:21]([C:23]4[S:27][C:26]([C:28]([O:30]C)=[O:29])=[CH:25][CH:24]=4)=[O:22])[CH2:15][CH2:16][CH2:17]2)[CH2:12]3)=[CH:4][CH:3]=1.[OH-].[Na+].Cl.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[CH:10][N:11]3[C:20]=2[CH:19]=[C:18]2[C@@:13]([CH3:32])([C@@H:14]([C:21]([C:23]4[S:27][C:26]([C:28]([OH:30])=[O:29])=[CH:25][CH:24]=4)=[O:22])[CH2:15][CH2:16][CH2:17]2)[CH2:12]3)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 311Citric AcidHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67448281methyl 5-((5aR,6S)-1-(4-fluorophenyl)-5a-methyl-5,5a,6,7,8,9-hexahydroimidazo[1,5-b]isoquinoline-6-carbonyl)thiophene-2-carboxylate

Product 1

HCID 674461785-((5aR,6S)-1-(4-fluorophenyl)-5a-methyl-5,5a,6,7,8,9-hexahydroimidazo[1,5-b]isoquinoline-6-carbonyl)thiophene-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of methyl 5-((5aR,6S)-1-(4-fluorophenyl)-5a-methyl-5,5a,6,7,8,9-hexahydroimidazo[1,5-b]isoquinoline-6-carbonyl)thiophene-2-carboxylate (110 mg, 0.24 mmol) in methanol (10 mL) was added aqueous sodium hydroxide solution (1 N, 2 mL, 2 mmol) dropwise followed by water (2 mL). The reaction mixture was stirred at RT for 15 min before neutralized with hydrochloric acid solution (6 N, 0.3 mL) and aqueous 10% citric acid solution. The mixture was concentrated under reduced pressure to remove methanol. The solid was filtered, washed with water, and dried to give 5-((5aR,6S)-1-(4-fluorophenyl)-5a-methyl-5,5a,6,7,8,9-hexahydroimidazo[1,5-b]isoquinoline-6-carbonyl)thiophene-2-carboxylic acid.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customto remove methanol
  3. filtrationThe solid was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-0369d46ccf434b85b03cdc0dfc04b5a2
Source dataset
uspto-grants-2012_11
Patent number
US08309730B2

Reaction notes

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