Isobutyl chloroformate → 5-(1-ethyl-2-pyrrolidinyl)methylcarbamoylspiro[benzo[b]furan-2(3H), 1'-cyclopropane]-3-one

HRID 894635Notes

Reaction equation

HRID 894635 reaction equation
[C:1]([C:4]1[CH:15]=[CH:14][C:7]2[O:8][C:9]3([C:12](=[O:13])[C:6]=2[CH:5]=1)[CH2:11][CH2:10]3)([OH:3])=O.C(Cl)(=O)OCC(C)C.[CH2:24]([N:26]1[CH2:30][CH2:29][CH2:28][CH:27]1[CH2:31][NH2:32])[CH3:25]>C(N(CC)CC)C>[CH2:24]([N:26]1[CH2:30][CH2:29][CH2:28][CH:27]1[CH2:31][NH:32][C:1]([C:4]1[CH:15]=[CH:14][C:7]2[O:8][C:9]3([C:12](=[O:13])[C:6]=2[CH:5]=1)[CH2:11][CH2:10]3)=[O:3])[CH3:25]

Participants

5

Reactant 3

HCID 62365Isobutyl chloroformateHCID 1172952-Aminomethyl-1-ethylpyrrolidineHCID 12926038HCID 12926038, compound

Product 1

HCID 127838615-(1-ethyl-2-pyrrolidinyl)methylcarbamoylspiro[benzo[b]furan-2(3H), 1'-cyclopropane]-3-oneYield 49.9%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

5-Carboxyspiro[benzo[b]furan-2(3H), 1'-cyclopropane]-3-one (2.04 g.), triethylamine (1.4 ml.), isobutyl chlorocarbonate (1.5 g.) and N-ethyl-2-aminomethylpyrrolidine (1.4 g.) were allowed to react in the same manner as Example 58. The product was converted to oxalate by a known procedure and recrystallization from ethanol gave colorless prisms of 5-(1-ethyl-2-pyrrolidinyl)methylcarbamoylspiro[benzo[b]furan-2(3H), 1'-cyclopropane]-3-one (1.567 g.).

Workup

  1. customto react in the same manner as Example 58
  2. customThe product was converted to oxalate by a known procedure and recrystallization from ethanol

Sources & evidence

ORD record
ord-5c7bf606fa5e442b93492872c857847b
Source dataset
uspto-grants-1981_08
Patent number
US04284644

Reaction notes

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