Lithium Chloride → HCID 67095564, compound

HRID 909030Notes

Reaction equation

HRID 909030 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([C:10]([N:12]2[CH2:16][C@@H:15]([CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])[C@@:14]([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=3[F:31])([C:22]#[N:23])[C@H:13]2[C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([Cl:38])[C:33]=2[F:39])=[O:11])=[CH:6][CH:5]=1.[BH4-].[Na+].[Li+].[Cl-]>CCO.C1COCC1>[Cl:38][C:34]1[C:33]([F:39])=[C:32]([CH:13]2[C:14]([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=3[F:31])([C:22]#[N:23])[CH:15]([CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:16][N:12]2[C:10](=[O:11])[C:7]2[CH:6]=[CH:5][C:4]([CH2:3][OH:2])=[CH:9][CH:8]=2)[CH:37]=[CH:36][CH:35]=1

Participants

6

Reactant 3

HCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 67095386HCID 67095386, compound

Product 1

HCID 67095564HCID 67095564, compoundYield 4.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of rac-4-[(2S,3S,4S)-2-(3-chloro-2-fluoro-phenyl)-3-(4-chloro-2-fluoro-phenyl)-3-cyano-4-(2,2-dimethyl-propyl)-pyrrolidine-1-carbonyl]-benzoic acid methyl ester (130.0 mg, 0.222 mmol) in EtOH (1.0 mL) and THF (1.0 mL) was added NaBH4 (36.0 mg, 0.96 mmol) and LiCl (40.7 mg, 0.96 mmol). The reaction mixture was stirred at rt overnight. Work up and the residue was purified by RP-HPLC to give rac-(2S,3S,4S)-2-(3-chloro-2-fluoro-phenyl)-3-(4-chloro-2-fluoro-phenyl)-4-(2,2-dimethyl-propyl)-1-(4-hydroxymethyl-benzoyl)-pyrrolidine-3-carbonitrile (5.7 mg, 4.6%). HRMS (ES+) m/z Calcd for C30H28Cl2F2N2O2+H [(M+H): 557.1568; Found: 557.1569.

Workup

  1. customthe residue was purified by RP-HPLC

Sources & evidence

ORD record
ord-199b7d8906414d308eba021a8606f01a
Source dataset
uspto-grants-2011_09
Patent number
US08017607B2

Reaction notes

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