Sodium borohydride → HCID 59201356, compound

HRID 451703Notes

Reaction equation

HRID 451703 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:20]=[C:21]([CH3:23])[CH:22]=1)[C:5]([C@@H:7]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8]1)=[O:6].[BH4-].[Na+]>CO>[F:1][C:2]1[CH:3]=[C:4]([C@H:5]([OH:6])[C@@H:7]2[CH2:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:18])([CH3:17])[CH3:19])=[O:14])[CH2:8]2)[CH:20]=[C:21]([CH3:23])[CH:22]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59201712HCID 59201712, compound

Product 1

HCID 59201356HCID 59201356, compoundYield 42.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (R)-tert-butyl 3-(3-fluoro-5-methylbenzoyl)piperidine-1-carboxylate (1.7 g, 5.3 mmol) in MeOH (30 mL), NaBH4 (1.61 g, 42.3 mmol) was added in portions and stirred overnight. The reaction was quenched with the addition of water (50 mL) and evaporated in vacuo until MeOH was removed. The aqueous layer was extracted with EA, washed with brine and dried over Na2SO4. The crude product was purified by chromatography to give (R)-tert-butyl 3-((R)-(3-fluoro-5-methylphenyl)(hydroxy)methyl)piperidine-1-carboxylate (730 mg, 42.9%).

Workup

  1. customThe reaction was quenched with the addition of water (50 mL)
  2. customevaporated in vacuo until MeOH
  3. customwas removed
  4. extractionThe aqueous layer was extracted with EA
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. customThe crude product was purified by chromatography

Sources & evidence

ORD record
ord-c0a6e4c00a8549fdb5a7f17e308dbf5f
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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