Sodium borohydride → Benzyl-(2,2-dimethoxy-1-methyl-ethyl)-amine

HRID 239126Notes

Reaction equation

HRID 239126 reaction equation
[BH4-].[Na+].[CH2:3]([N:10]=[C:11]([CH3:17])[CH:12]([O:15][CH3:16])[O:13][CH3:14])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CO>[CH2:3]([NH:10][CH:11]([CH3:17])[CH:12]([O:15][CH3:16])[O:13][CH3:14])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 71380533N-(1,1-Dimethoxypropan-2-ylidene)-1-phenylmethanamine

Product 1

HCID 12293011Benzyl-(2,2-dimethoxy-1-methyl-ethyl)-amineYield 56.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3.95 g sodium borohydride was added to 18.9 g benzyl-(2,2-dimethoxy-1-methyl-ethylidene)-amine in 100 mL methanol at 0-5° C. The reaction was stirred over night at RT. The solvent was removed, dissolved in toluol and washed with water and saturated ammoniumchloride solution. The organic layer was evaporated and the residue was purified by column chromatographie on silica gel (cyclohexane/ethylacetate) to give 10.7 g of the desired product.

Workup

  1. customThe solvent was removed
  2. dissolutiondissolved in toluol
  3. washwashed with water and saturated ammoniumchloride solution
  4. customThe organic layer was evaporated
  5. customthe residue was purified by column chromatographie on silica gel (cyclohexane/ethylacetate)

Sources & evidence

ORD record
ord-55d8e6d831c94dc9a1b1cfb5ac7b890a
Source dataset
uspto-grants-2014_02
Patent number
US08642774B2

Reaction notes

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