Benzyl chloroformate → 2-Amino-2-methyl-1-propyl acetate hydrochloride

HRID 372838Notes

Reaction equation

HRID 372838 reaction equation
C([Cl:11])([O:3][CH2:4][C:5]1C=CC=CC=1)=O.[NH2:12][C:13]([CH3:17])([CH3:16])[CH2:14][OH:15]>ClCCl>[ClH:11].[C:4]([O:15][CH2:14][C:13]([NH2:12])([CH3:17])[CH3:16])(=[O:3])[CH3:5]

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 118072-Amino-2-methyl-1-propanol

Product 1

HCID 123255442-Amino-2-methyl-1-propyl acetate hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a dichloromethane solution containing 17.1 g (0.1 mol) carbobenzoxychloride at 0° was added dropwise with stirring 18.4 g (0.2 mol) 2-amino-2-methyl-1-propanol. The reaction mixture was stirred at room temperature overnight and the 2-amino-2-methyl-1-propanol hydrochloride which formed was removed by filtration. Removal of the dichloromethane under reduced pressure afforded a colorless, viscous liquid. Distillation gave 14.9 g (0.07 mol), 70%, 2-carbobenzoxyamino-2-methyl-1-propanol, bp 144°-148° (0.3 mm); ir (neat) 3400, 3020, 2980, 1710, 1510, 1455, 1270, 1070, 730 and 680 cm-1 ; pmr (CDCl3) δ 7.2 (s, 5H), 5.4 (bs, 1H), 4.9 (s, 2H), 4.2 (bs, 1H), 3.4 (s, 2H) and 1.2 (s, 6H) ppm.

Workup

  1. additionwas added dropwise

Sources & evidence

ORD record
ord-aaa23bf906c1491db3dab712c1955777
Source dataset
uspto-grants-1978_05
Patent number
US04092420

Reaction notes

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