(R)-1-(3-chlorophenyl)ethanamine → HCID 25265629, compound

HRID 2194839Notes

Reaction equation

HRID 2194839 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:15][C:16]1[CH:17]=[C:18]([C@H:22]([NH2:24])[CH3:23])[CH:19]=[CH:20][CH:21]=1.[F:25][C:26]1[CH:31]=[CH:30][C:29]([N:32]2[C:36](=[O:37])[CH2:35][CH:34]([CH:38]=O)[CH2:33]2)=[CH:28][CH:27]=1>CC(O)=O.ClCCCl>[Cl:15][C:16]1[CH:17]=[C:18]([C@H:22]([NH:24][CH2:38][CH:34]2[CH2:33][N:32]([C:29]3[CH:30]=[CH:31][C:26]([F:25])=[CH:27][CH:28]=3)[C:36](=[O:37])[CH2:35]2)[CH3:23])[CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 3

HCID 2507697(R)-1-(3-chlorophenyl)ethanamineHCID 5049666Sodium triacetoxyborohydrideHCID 58360599HCID 58360599, compound

Product 1

HCID 25265629HCID 25265629, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 111,2-DichloroethaneSolvent

Procedure

A 20 mL vial was charged with sodium triacetoxyborohydride (1.0 g, 4.8 mmol), (R)-1-(3-chlorophenyl)ethanamine 55 (0.413 g, 2.7 mmol), 1-(4-fluorophenyl)-5-oxopyrrolidine-3-carbaldehyde 54 (0.500 g, 2.4 mmol), 10 mL of DCE, and 5 drops of AcOH. This mixture was stirred at room temperature overnight then quenched with saturated aqueous NaHCO3. The mixture was extracted with DCM, dried, concentrated, and purified by column chromatography on silica gel (3% to 7% MeOH in DCM) to give 4-({[(1R)-1-(3-chlorophenyl)ethyl]amino}methyl)-1-(4-fluorophenyl)pyrrolidin-2-one 56 as a 1:1 mixture of diastereomers. Mass spectrum: calculated for C19H20ClFN2O 346.1; found 347.2 (M++1).

Workup

  1. customthen quenched with saturated aqueous NaHCO3
  2. extractionThe mixture was extracted with DCM
  3. customdried
  4. concentrationconcentrated
  5. custompurified by column chromatography on silica gel (3% to 7% MeOH in DCM)

Sources & evidence

ORD record
ord-916930dc8aa449ff9f79263ffc089996
Source dataset
uspto-grants-2012_12
Patent number
US08334317B2

Reaction notes

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