Dichloromethane → HCID 58136752, compound

HRID 877243Notes

Reaction equation

HRID 877243 reaction equation
[CH:1]1([CH:6]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][N:21]3[C:29](=[O:30])[C:28]4[C:23](=[C:24]([F:32])[CH:25]=[CH:26][C:27]=4[F:31])[C:22]3=[O:33])=[CH:16][CH:15]=2)[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+].ClCCl>C(O)C>[CH:1]1([CH:6]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][N:21]3[C:22](=[O:33])[C:23]4[C:28](=[C:27]([F:31])[CH:26]=[CH:25][C:24]=4[F:32])[CH:29]3[OH:30])=[CH:16][CH:15]=2)[C:7]([O:9][C:10]([CH3:12])([CH3:11])[CH3:13])=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 58136579HCID 58136579, compound

Product 1

HCID 58136752HCID 58136752, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 200.0 mg (0.44 mmol) of tert-butyl(+/−)-cyclopentyl{4-[(4,7-difluoro-1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}acetate in 1 ml of ethanol was cooled to 0° C., and 18.3 mg (0.48 mmol) of sodium borohydride were added. 0.2 ml of dichloromethane was added, and the reaction mixture was warmed to RT. After 1 h of stirring, the mixture was concentrated and the residue was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 6:1 to 4:1). This gave 182 mg (90.6% of theory) of the target compound.

Workup

  1. concentrationthe mixture was concentrated
  2. customthe residue was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 6:1 to 4:1)

Sources & evidence

ORD record
ord-f685001ce68a44619b4025f07e90117a
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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