Sodium borohydride → HCID 23003703, compound

HRID 396300Notes

Reaction equation

HRID 396300 reaction equation
[BH4-].[Na+].[CH2:3]([N:10]1[CH2:15][CH2:14][C:13](=[O:16])[CH:12]([C:17]([F:20])([F:19])[F:18])[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CO>[CH2:3]([N:10]1[CH2:15][CH2:14][CH:13]([OH:16])[CH:12]([C:17]([F:20])([F:18])[F:19])[CH2:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 23003695HCID 23003695, compound

Product 1

HCID 23003703HCID 23003703, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (0.6 g, 16.0 mmole) was added to the stirred solution of 1-benzyl-3-trifluoromethylpiperidin-4-one (2.1 g, 8.2 mmole) in methanol (25 ml) at 0-5° C. over a period of 5 min, and stirring was continued for 2 hr at ambient temperature. The reaction mixture was concentrated to dryness, triturated with water (20 ml) and extracted with chloroform. The chloroform extract was dried over sodium sulphate and concentrated to dryness to furnish 1-benzyl-4-hydroxy-3-trifluoromethylpiperidine as oil. Yield 1.8 g (85%), C13H16F3NO, m/z 259 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customtriturated with water (20 ml)
  3. extractionextracted with chloroform
  4. extractionThe chloroform extract
  5. dry with materialwas dried over sodium sulphate
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-23e1ecd6081d486199191f55ef644b61
Source dataset
uspto-grants-2003_08
Patent number
US06608078B2

Reaction notes

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