Sodium borohydride → HCID 23003686, compound

HRID 396312Notes

Reaction equation

HRID 396312 reaction equation
[BH4-].[Na+].[CH2:3]([N:10]1[CH2:15][CH2:14][C:13](=[O:16])[C:12]([CH2:18][CH3:19])([CH3:17])[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]([CH2:18][CH3:19])([CH3:17])[CH2:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 22278904HCID 22278904, compound

Product 1

HCID 23003686HCID 23003686, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (0.3 g, 9.0 mmole) was added to the stirred solution of the 1-benzyl-3-ethyl-3-methylpiperid-4-one (1.5 g, 6.5 mmole) in methanol (20 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 ethyl acetate (2×50 ml). The extract was dried over sodium sulphate and concentrated to dryness to furnish 1-benzyl-3-ethyl-4-hydroxy-3-methylpiperidine product as oil, which was used as such in the next step. Yield 1.1 g (74%), C15H23NO, m/z 234 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customtriturated with water (20 ml)
  3. extractionextracted with ethyl acetate (2×50 ml)
  4. dry with materialThe extract was dried over sodium sulphate
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-5535690c20dc438698ef8700252ad955
Source dataset
uspto-grants-2003_08
Patent number
US06608078B2

Reaction notes

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