2-Amino-1-butanol → (1r)-1-Bromocyclopropanecarboxylic acid-2-hydroxy-1-ethylethylamide

Reaction equation

[OH:1][CH2:2][C@H:3]([NH:10][C:11]([C:13]1([Br:16])[CH2:15][CH2:14]1)=[O:12])[C:4]1C=CC=C[CH:5]=1.BrC1(C(Cl)=O)CC1.NC(CC)CO>>[OH:1][CH2:2][C@H:3]([NH:10][C:11]([C:13]1([Br:16])[CH2:15][CH2:14]1)=[O:12])[CH2:4][CH3:5]

Participants

Reactant 3

HCID 221292-Amino-1-butanol

HCID 109102061-Bromocyclopropane-carboxylic acid chloride

HCID 21350875(IR)-1-bromocyclopropanecarboxylic acid-2-hydroxy-1-phenylethylamide

Product 1

HCID 21350874(1r)-1-Bromocyclopropanecarboxylic acid-2-hydroxy-1-ethylethylamide

Procedure

Analogously to the production of amide 110, 2.18 g of acid chloride 107 is reacted with 962 mg of (−)-2-amino-1-butanol, whereby 2.3 g of (1R)-1-bromocyclopropanecarboxylic acid-2-hydroxy-1-ethylethylamide 114 is obtained as a colorless oil.

Sources & evidence

ORD record: ord-59df5f8e3a144d6787180caabb46535d
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06642218B2

Reaction notes

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