Lithium borohydride → HCID 67327561, compound

HRID 1880207Notes

Reaction equation

HRID 1880207 reaction equation
C([O:3][C:4]([CH:6]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)[CH2:9][N:8]([C:19]([N:21]2[CH2:26][CH2:25][N:24]([S:27]([CH3:30])(=[O:29])=[O:28])[CH2:23][CH2:22]2)=[O:20])[CH2:7]1)=O)C.[Li+].[BH4-]>CO>[Cl:18][C:13]1[CH:12]=[C:11]([CH:10]2[CH:6]([CH2:4][OH:3])[CH2:7][N:8]([C:19]([N:21]3[CH2:22][CH2:23][N:24]([S:27]([CH3:30])(=[O:28])=[O:29])[CH2:25][CH2:26]3)=[O:20])[CH2:9]2)[CH:16]=[CH:15][C:14]=1[Cl:17]

Participants

4

Reactant 2

HCID 4148881Lithium borohydride2×HCID 67328669HCID 67328669, compound

Product 1

HCID 67327561HCID 67327561, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of (3SR,4RS)-4-(3,4-dichloro-phenyl)-1-(4-methanesulfonyl-piperazine-1-carbonyl)-pyrrolidine-3-carboxylic acid ethyl ester (2.39 g, 5.00 mmol) in MeOH (80 mL) at RT was added LiBH4 (434 mg, 19.9 mmol). After 2 hours a second portion of LiBH4 (1.30 g, 59.7 mmol) was added and stirring was continued for 2 days. The reaction mixture was poured on H2O, extracted with EtOAc and the combined organic phases were dried over Na2SO4. Flash chromatography (SiO2, EtOAc, then EtOAc/MeOH 9:1) yielded the title product (1.76 g, 81%) as a white solid. ES-MS m/e: 436.1 (M+H+).

Workup

  1. additionThe reaction mixture was poured on H2O
  2. extractionextracted with EtOAc
  3. dry with materialthe combined organic phases were dried over Na2SO4

Sources & evidence

ORD record
ord-0257d9446df348cba82be759dc810107
Source dataset
uspto-grants-2012_11
Patent number
US08318759B2

Reaction notes

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