Dicyclohexylcarbodiimide → 1-bromo-N-[(1-hydroxymethyl)propyl]-cyclopropane-1-carboxamide

HRID 478156Notes

Reaction equation

HRID 478156 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[Br:16][C:17]1([C:20]([OH:22])=O)[CH2:19][CH2:18]1.O[N:24]1[C:28](=[O:29])[CH2:27][CH2:26][C:25]1=O.NC(CC)CO>C(Cl)Cl>[Br:16][C:17]1([C:20]([NH:24][CH2:25][CH2:26][CH2:27][CH2:28][OH:29])=[O:22])[CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 221292-Amino-1-butanolHCID 80170N-HydroxysuccinimideHCID 128674801-Bromocyclopropane-1-carboxylic acid

Product 1

HCID 694261281-bromo-N-[(1-hydroxymethyl)propyl]-cyclopropane-1-carboxamideYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7.45 g of N,N′-dicyclohexylcarbodiimide is added at 0° C. under nitrogen to a solution of 5.0 g of 1-bromocyclopropanecarboxylic acid 4 and 4.18 g of N-hydroxysuccinimide in 87 ml of methylene chloride, and it is stirred for 1.5 more hours. Then, 7.46 ml of 2-amino-1-butanol is added, and it is stirred for 2 hours at room temperature. After dilution with methylene chloride, it is filtered, concentrated by evaporation, and the residue is chromatographed on silica gel with ethyl acetate/hexane. 5.44 g of 1-bromo-N-[(1-hydroxymethyl)propyl]-cyclopropane-1-carboxamide 78 is obtained as a yellowish oil.

Workup

  1. stirringit is stirred for 2 hours at room temperature
  2. filtrationAfter dilution with methylene chloride, it is filtered
  3. concentrationconcentrated by evaporation
  4. customthe residue is chromatographed on silica gel with ethyl acetate/hexane

Sources & evidence

ORD record
ord-63594326eaa74d6bba4a48cddb098dc4
Source dataset
uspto-grants-2003_11
Patent number
US06642218B2

Reaction notes

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