Sodium borohydride → HCID 23003716, compound

HRID 396306Notes

Reaction equation

HRID 396306 reaction equation
[BH4-].[Na+].[CH2:3]([N:10]1[CH2:15][CH2:14][C:13](=[O:16])[C:12]([CH2:19][CH3:20])([CH2:17][CH3:18])[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])[C:12]([CH2:19][CH3:20])([CH2:17][CH3:18])[CH2:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 22278925HCID 22278925, compound

Product 1

HCID 23003716HCID 23003716, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (0.3 g, 8.13 mmole) was added to the stirred solution of 1-benzyl-3,3-diethylpiperidin-4-one (4.0 g, 16.26 mmole) in methanol (22 ml) at 0-5° C. over a period of 15 min, and stirring was continued for 30 min. The reaction mixture was concentrated to dryness, triturated with water (25 ml) and extracted with ethyl acetate (2×100 ml). The extract was dried (sodium sulphate) and concentrated to dryness to furnish 1-benzyl-3,3-diethyl-4-hydroxy-piperidine as oil. Yield 3.9 g (97%), C16H24NO, m/z 248 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customtriturated with water (25 ml)
  3. extractionextracted with ethyl acetate (2×100 ml)
  4. dry with materialThe extract was dried (sodium sulphate)
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-18418a8f088b49ad8d2d6e5ae6f2f571
Source dataset
uspto-grants-2003_08
Patent number
US06608078B2

Reaction notes

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