Benzyl chloroformate → 5-benzyloxycarbonylaminospiro[benzo[b]furan-2(3H), 1'-cyclopropane]-3-one

HRID 894618Notes

Reaction equation

HRID 894618 reaction equation
[NH2:1][C:2]1[CH:13]=[CH:12][C:5]2[O:6][C:7]3([C:10](=[O:11])[C:4]=2[CH:3]=1)[CH2:9][CH2:8]3.[C:14](Cl)([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15]>N1C=CC=CC=1>[CH2:17]([O:16][C:14]([NH:1][C:2]1[CH:13]=[CH:12][C:5]2[O:6][C:7]3([C:10](=[O:11])[C:4]=2[CH:3]=1)[CH2:9][CH2:8]3)=[O:15])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 12925991HCID 12925991, compound

Product 1

HCID 129259985-benzyloxycarbonylaminospiro[benzo[b]furan-2(3H), 1'-cyclopropane]-3-one

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 5-aminospiro[benzo[b]furan-2(3H), 1'-cyclopropane]-3-one (1.35 g.) in pyridine (13.5 ml.) was added carbobenzyloxy chloride (30% toluene solution, 7 g.) under ice-cooling, and the mixture stirred for one hour. The reaction mixture was poured into ice-hydrochloric acid (14 ml.) and extracted with ethyl acetate. The extract was washed with water, dried and concentrated to remove the solvent. The residue was recrystallized from ethanol. By the above procedure there was obtained 5-benzyloxycarbonylaminospiro[benzo[b]furan-2(3H), 1'-cyclopropane]-3-one as pale yellow needles, m.p. 118°-119° C. Yield 1.57 g.

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customto remove the solvent
  7. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-cd7e0b0436c54ed685bc6dfcccb3b37d
Source dataset
uspto-grants-1981_08
Patent number
US04284644

Reaction notes

Loading…