tert-Butanol → Tert-butyl 3-amino-3-phenylpropanoate

HRID 341764Notes

Reaction equation

HRID 341764 reaction equation
[C:1]1([CH:7]2[NH:10][C:9](=[O:11])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[Si](C)(C)C.[C:17]([OH:21])([CH3:20])([CH3:19])[CH3:18]>>[C:1]1([CH:7]([NH2:10])[CH2:8][C:9]([O:21][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 6386tert-ButanolHCID 6397ChlorotrimethylsilaneHCID 5688184-Phenylazetidin-2-one

Product 1

HCID 14557402Tert-butyl 3-amino-3-phenylpropanoateYield 47%

Procedure

A solution of 10 g of 4-phenylazetidin-2-one and 15.2 g of chlorotrimethylsilane in 150 cm3 of anhydrous tert.-butanol are refluxed for 7 days. The solution is then evaporated and ethyl acetate and aqueous sodium bicarbonate at 5% are added. The organic phase is washed with water, dried on sodium sulphate and is then evaporated. 7 g of tert.- butyl 3-phenyl-3-amino-propanoate are obtained (yield 47%).

Workup

  1. customThe solution is then evaporated
  2. additionethyl acetate and aqueous sodium bicarbonate at 5% are added
  3. washThe organic phase is washed with water
  4. customdried on sodium sulphate
  5. customis then evaporated

Sources & evidence

ORD record
ord-c7f4b938f8e446de88aeea24dd7b13c0
Source dataset
uspto-grants-1999_01
Patent number
US05856311

Reaction notes

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