Ethanolamine → benzyl N-(2-hydroxyethyl)carbamate

HRID 613210Notes

Reaction equation

HRID 613210 reaction equation
[NH2:1][CH2:2][CH2:3][OH:4].Cl[C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7]>C(Cl)Cl>[C:6]([NH:1][CH2:2][CH2:3][OH:4])([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 10387Benzyl chloroformate

Product 1

HCID 280458benzyl N-(2-hydroxyethyl)carbamateYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 0° C. cold of CH2Cl2 solution (300 mL) of 2-aminoethanol (10.8 g, 0.177 mole) and TEA (26.8 g; 0.265 mole) was added slowly a CH2Cl2 solution (50 mL) of benzyl chloroformate (33.2 g, 0.194 mole). After complete addition, the resulting solution was gradually warmed to room temperature and stirring was continued at room temperature overnight. The reaction was worked up and purified by flash column chromatography on silica gel, affording 22.8 g in 66% yield of title compound. 1H NMR (CDCl3): δ 7.34-7.40 (m, 5H), 5.20-5.32 (m, 1H), 5.14 (s, 2H), 3.74 (q, 2H), 3.37 (q, 2H), 2.38 (bs, 1H).

Workup

  1. additionAfter complete addition
  2. custompurified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-de9d4e85ecac40b3961ab37b8d363f07
Source dataset
uspto-grants-1999_12
Patent number
US06007992

Reaction notes

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