Sodium borohydride → 1-Benzyl-3-cyano-4-hydroxypiperidine

HRID 396329Notes

Reaction equation

HRID 396329 reaction equation
[BH4-].[Na+].[CH2:3]([N:10]1[CH2:15][CH2:14][C:13](=[O:16])[CH:12]([C:17]#[N:18])[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(O)C>[CH2:3]([N:10]1[CH2:15][CH2:14][CH:13]([OH:16])[CH:12]([C:17]#[N: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 230037231-Benzyl-4-oxopiperidine-3-carbonitrile

Product 1

HCID 230037331-Benzyl-3-cyano-4-hydroxypiperidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (0.89 g, 23.37 mmole) was added to the stirred solution of 1-benzyl-3-cyanopiperidin-4-one (2.5 g, 11.68 mmole) in ethanol (125 ml) at 0° C. over a period of 30 min, and stirring was continued for 2 hr at 5° C. The reaction mixture was concentrated to dryness, triturated with water (20 ml) and extracted with ethyl acetate. The extract was concentrated to dryness to furnish 1-benzyl-3-cyano-4-hydroxypiperidine product as oil. Yield 1.85 g (73%) C13H16N2O, m/z 217 (M+1), PMR (CDCl3): 1.78 (2H, m, H5), 2.22 (1H, m, H3), 2.6-3.12 (4H, m, H2 & H6), 3.58 (1H, m, H4), 3.65 (2H, s, CH2—Ar), 7.32 (5H, s, ArH).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customtriturated with water (20 ml)
  3. extractionextracted with ethyl acetate
  4. concentrationThe extract was concentrated to dryness

Sources & evidence

ORD record
ord-f1586bdc0e8f4616bd68a5cc3fe3c191
Source dataset
uspto-grants-2003_08
Patent number
US06608078B2

Reaction notes

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