Sodium borohydride → 5-(3,4-Difluorophenyl)-7-hydroxyhexahydroindolizin-3-one

HRID 553873Notes

Reaction equation

HRID 553873 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([CH:11]2[CH2:19][C:18](=[O:20])[CH2:17][CH:16]3[N:12]2[C:13](=[O:21])[CH2:14][CH2:15]3)[CH:7]=[CH:8][C:9]=1[F:10]>C(O)C>[F:3][C:4]1[CH:5]=[C:6]([CH:11]2[CH2:19][CH:18]([OH:20])[CH2:17][CH:16]3[N:12]2[C:13](=[O:21])[CH2:14][CH2:15]3)[CH:7]=[CH:8][C:9]=1[F:10]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 674649855-(3,4-Difluorophenyl)hexahydroindolizine-3,7-dione

Product 1

HCID 674649235-(3,4-Difluorophenyl)-7-hydroxyhexahydroindolizin-3-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (644 mg) was added to a solution of 5-(3,4-difluorophenyl)hexahydroindolizine-3,7-dione obtained above (1.4 g) in ethanol (20 mL) at room temperature, and the reaction solution was stirred for one hour. The reaction solution was added to ice water, followed by extraction with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain 1.5 g of the title compound. The property value of the compound is as follows.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8ce248c4f2284012aed95fc3b3b52ee4
Source dataset
uspto-grants-2011_11
Patent number
US08048878B2

Reaction notes

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