Sodium borohydride → 4-(Aminomethyl)oxane-4-carbonitrile

HRID 1963832Notes

Reaction equation

HRID 1963832 reaction equation
[O:1]1[CH2:6][CH2:5][C:4]([C:9]#[N:10])([C:7]#[N:8])[CH2:3][CH2:2]1.[BH4-].[Na+]>CCO>[NH2:10][CH2:9][C:4]1([C:7]#[N:8])[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 14537194Dihydro-2H-pyran-4,4(3H)-dicarbonitrile

Product 1

HCID 552854014-(Aminomethyl)oxane-4-carbonitrileYield 83.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of dihydro-2H-pyran-4,4(3H)-dicarbonitrile (450 mg, 3.31 mmol) and Sodium borohydride (375 mg, 9.92 mmol) in EtOH (15 ml) was stirred at ambient temperature for about 4 hours. The mixture was concentrated and the resulting residue was diluted with ethyl acetate, washed with water and dried. Concentration in vacuo afforded 388 mg of the crude product which was used directly in the next step. LCMS (m/z): 141.0 [M+H]+; Retention time=0.18 min.

Workup

  1. concentrationThe mixture was concentrated
  2. additionthe resulting residue was diluted with ethyl acetate
  3. washwashed with water
  4. customdried
  5. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-7a762b65928d490e825c743da241f99e
Source dataset
uspto-grants-2013_04
Patent number
US08415381B2

Reaction notes

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