Sodium borohydride → 4-(Benzylamino)-1,1-dimethoxybutan-2-ol

HRID 526731Notes

Reaction equation

HRID 526731 reaction equation
[CH2:1]([NH:8]/[CH:9]=[CH:10]/[C:11](=[O:17])[CH:12]([O:15][CH3:16])[O:13][CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CC(O)C.O>[CH2:1]([NH:8][CH2:9][CH2:10][CH:11]([OH:17])[CH:12]([O:15][CH3:16])[O:13][CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 89315947(E)-4-(benzylamino)-1,1-dimethoxybut-3-en-2-one

Product 1

HCID 893159194-(Benzylamino)-1,1-dimethoxybutan-2-olYield 74.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

To a solution of (E)-4-(benzylamino)-1,1-dimethoxybut-3-en-2-one (4.71 g, 20 mmol) in a mixture of 2-Propanol (60 ml) and Water (4.80 ml) was added sodium borohydride (3.03 g, 80 mmol) in portions at 20-25° C., the mixture was stirred overnight. Quenched with 5N HCl to pH 7 (approx 10 ml), pH adjusted to 8-9 with 5N NaOH, diluted with MTBE (100 ml) and brine (50 ml). Organic phase was dried (MgSO4), evaporated, separated on a column with ethyl acetate-MeOH mixture 4:1, fractions collected to give 4-(benzylamino)-1,1-dimethoxybutan-2-ol (3.55 g, 14.83 mmol, 74.2% yield), colorless oil.

Workup

  1. customQuenched with 5N HCl to pH 7 (approx 10 ml)
  2. additiondiluted with MTBE (100 ml) and brine (50 ml)
  3. dry with materialOrganic phase was dried (MgSO4)
  4. customevaporated
  5. customseparated on a column with ethyl acetate-MeOH mixture 4:1, fractions
  6. customcollected

Sources & evidence

ORD record
ord-8667c2e4cc8a497b950ba318b6bffd33
Source dataset
uspto-grants-2016_05
Patent number
US09346751B2

Reaction notes

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