Ethyl Acetate → benzyl N-(1-hydroxy-2-methylpropan-2-yl)carbamate

HRID 2294360Notes

Reaction equation

HRID 2294360 reaction equation
[NH2:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4].[CH2:7]([O:14][C:15](Cl)=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>O>[CH2:7]([O:14][C:15]([NH:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4])=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 118072-Amino-2-methyl-1-propanol

Product 1

HCID 12325553benzyl N-(1-hydroxy-2-methylpropan-2-yl)carbamateYield 100.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A procedure similar to that described in Preparation 7 was repeated, except that 7.00 g of 2-amino-2-methylpropanol, 13.47 g of benzyloxycarbonyl chloride, 13.13 g of potassium carbonate, 35 ml of ethyl acetate and 35 ml of water were used, to give 17.59 g of the title compound having an Rf value of 0.72 (on silica gel thin layer chromatography, using a 3:1 by volume mixture of ethyl acetate and hexane as the developing solvent).

Workup

  1. customA procedure similar to that described in Preparation 7

Sources & evidence

ORD record
ord-4da3faef15b44053bbe42775d42aa27f
Source dataset
uspto-grants-1997_11
Patent number
US05688823

Reaction notes

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