Sodium borohydride → Allyl-(2,2-dimethyl-pent-4-enyl)-amine

HRID 751462Notes

Reaction equation

HRID 751462 reaction equation
[CH2:1]([N:4]=[CH:5][C:6]([CH3:11])([CH3:10])[CH2:7][CH:8]=[CH2:9])[CH:2]=[CH2:3].[BH4-].[Na+]>CO>[CH2:1]([NH:4][CH2:5][C:6]([CH3:11])([CH3:10])[CH2:7][CH:8]=[CH2:9])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 22928390Allyl-(2,2-dimethyl-pent-4-enylidene)-amine

Product 1

HCID 11126468Allyl-(2,2-dimethyl-pent-4-enyl)-amineYield 59%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Allyl-(2,2-dimethyl-pent-4-enylidene)-amine of Example 92a (3.76 g, 25 mmol) was diluted in 5 ml MeOH. To the solution NaBH4 (0.95 g, 25 mmol) was added at 0° C. After addition the mixture was stirred at r.t. for 5 h. Methanol was removed on rotavapor and the residue was partitioned between EtOAc/20% NaOH. The organic layer was dried over Na2SO4, fitered and evaperated to give 2.26 g of the title compound: MS (M+H+): 154.0; 1H-NMR (400 MHz, CDCl3): 5.93-5.76(m, 2H), 5.29-4.99(m, 4H), 3.22(d, 2H), 2.34(s, 2H), 2.01(d, 2H), 0.94(s, 6H).

Workup

  1. additionAfter addition the mixture
  2. customMethanol was removed on rotavapor
  3. customthe residue was partitioned between EtOAc/20% NaOH
  4. dry with materialThe organic layer was dried over Na2SO4

Sources & evidence

ORD record
ord-024886c06014479d87f2489ecd14931b
Source dataset
uspto-grants-2008_07
Patent number
US07405209B2

Reaction notes

Loading…