Lithium borohydride → HCID 67327277, compound

HRID 1158644Notes

Reaction equation

HRID 1158644 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:13][N:12]([C:14]([N:16]3[CH2:21][CH2:20][N:19]([S:22]([CH3:25])(=[O:24])=[O:23])[CH2:18][CH2:17]3)=[O:15])[CH2:11][CH:10]2[C:26](=[O:28])[CH3:27])[CH:5]=[CH:6][C:7]=1[Cl:8].[Li+].[BH4-]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH:10]([CH:26]([OH:28])[CH3:27])[CH2:11][N:12]([C:14]([N:16]3[CH2:17][CH2:18][N:19]([S:22]([CH3:25])(=[O:23])=[O:24])[CH2:20][CH2:21]3)=[O:15])[CH2:13]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 67328162HCID 67328162, compound

Product 1

HCID 67327277HCID 67327277, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 1-[(3SR,4RS)-4-(3,4-dichloro-phenyl)-1-(4-methanesulfonyl-piperazine-1-carbonyl)-pyrrolidin-3-yl]-ethanone (XI-1) (2.00 g, 4.46 mmol) in MeOH (40 mL) at −78° C. was added LiBH4 (0.13 g, 4.68 mmol). The temperature was slowly raised to RT (over 1 hour), and the reaction mixture was quenched by addition of H2O. The product was extracted with EtOAc, the combined organic phases were dried over Na2SO4. The two diastereoisomers were separated by column chromatography (SiO2) to yield 0.31 g (16%) of [(3RS,4SR)-3-(3,4-dichloro-phenyl)-4-((RS)-1 hydroxy-ethyl)-pyrrolidin-1-yl]-(4-methanesulfonyl-piperazin-1-yl)-methanone (XII-A-1) as a white solid ES-MS m/e: 450.1 (M+Ht) and 1.02 g (51%) of [(3RS,4SR)-3-(3,4-dichloro-phenyl)-4-((SR)-1-hydroxy-ethyl)-pyrrolidin-1-yl]-(4 methanesulfonyl-piperazin-1-yl)-methanone (XII-1-B-1) as a white solid ES-MS m/e: 450.1 (M+H+).

Workup

  1. customthe reaction mixture was quenched by addition of H2O
  2. extractionThe product was extracted with EtOAc
  3. dry with materialthe combined organic phases were dried over Na2SO4
  4. customThe two diastereoisomers were separated by column chromatography (SiO2)

Sources & evidence

ORD record
ord-2326833b59d24a6fbde0aaf9f5e169d6
Source dataset
uspto-grants-2010_10
Patent number
US07812021B2

Reaction notes

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