Sodium borohydride → HCID 49760120, compound

HRID 713183Notes

Reaction equation

HRID 713183 reaction equation
[F:1][C:2]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:3]=1[C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)=[O:5].[BH4-].[Na+]>CO>[F:1][C:2]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:3]=1[CH:4]([OH:5])[CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[O:13])[CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 49760095tert-Butyl 4-(2,4-difluorobenzoyl)piperidine-1-carboxylate

Product 1

HCID 49760120HCID 49760120, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 0° C. solution of tert-butyl 4-(2,4-difluorobenzoyl)piperidine-1-carboxylate (1.28 g, 3.93 mmol) in MeOH (15.7 mL) was added NaBH4 (0.372 g, 9.84 mmol). The ice bath was removed and the reaction mixture stirred for 2 h at room temperature then was quenched with saturated aqueous NH4Cl. The organic layer was extracted with EtOAc, washed with H2O and dried over MgSO4. The solvent was removed under reduced pressure gave tert-butyl 4-((2,4-difluorophenyl)(hydroxy)methyl)piperidine-1-carboxylate as a white hygroscopic solid.

Workup

  1. customThe ice bath was removed
  2. customthen was quenched with saturated aqueous NH4Cl
  3. extractionThe organic layer was extracted with EtOAc
  4. washwashed with H2O
  5. dry with materialdried over MgSO4
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-982a4f4aff0b4771b17ddf158a892c31
Source dataset
uspto-grants-2015_11
Patent number
US09181249B2

Reaction notes

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