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

HRID 1623251Notes

Reaction equation

HRID 1623251 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)<autotext key=“0BD391A6” name=“[Reactants]” index=“1” field=“Reactants” type=“field” length=“34”/> and Sodium borohydride (375 mg, 9.92 mmol)<autotext key=“0BD391A7” name=“[Reactants]” index=“2” field=“Reactants” type=“field” length=“38”/> in EtOH (15 ml)<autotext key=“0BD391A8” name=“[Solvents]” index=“l” field=“Solvents” type=“field” length=“12”/> 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-b0c14254e376437daa3b41ee06a3eff9
Source dataset
uspto-grants-2014_07
Patent number
US08778951B2

Reaction notes

Loading…