Ethanolamine → 1-Boc-3-[(2-hydroxyethyl)amino]-azetidine

Reaction equation

[C:1]([N:8]1[CH2:11][C:10](=O)[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:13]([CH2:15][NH2:16])[OH:14]>>[C:1]([N:8]1[CH2:11][CH:10]([NH:16][CH2:15][CH2:13][OH:14])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

Reactant 2

HCID 700Ethanolamine

HCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 592849281-Boc-3-[(2-hydroxyethyl)amino]-azetidineYield 62.3%

Procedure

N-Boc-3-azetidinone (1.0 g, 5.84 mmol) was treated with ethanolamine following Procedure 1-Method A to yield N-(N-Boc-azetidin-3-yl)-2-amino-ethanol (0.75 g, 3.46 mmol, 62.3% yield): MS m/e [M+H]+ calcd 217.1, found 217.2.

Sources & evidence

ORD record: ord-93acec3625d84ebd8b25a7cc2ec25b41
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383596B2

Reaction notes

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