Allyl chloroformate → Tert-butyl 4-(1-allyloxycarbonylaminocyclopropyl)benzoate

HRID 2240635Notes

Reaction equation

HRID 2240635 reaction equation
[NH2:1][C:2]1([C:5]2[CH:17]=[CH:16][C:8]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:7][CH:6]=2)[CH2:4][CH2:3]1.Cl[C:19]([O:21][CH2:22][CH:23]=[CH2:24])=[O:20]>ClCCl.N1C=CC=CC=1>[CH2:22]([O:21][C:19]([NH:1][C:2]1([C:5]2[CH:17]=[CH:16][C:8]([C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])=[CH:7][CH:6]=2)[CH2:4][CH2:3]1)=[O:20])[CH:23]=[CH2:24]

Participants

5

Reactant 2

HCID 18052Allyl chloroformateHCID 59305811Tert-butyl 4-(1-aminocyclopropyl)benzoate

Product 1

HCID 59305799Tert-butyl 4-(1-allyloxycarbonylaminocyclopropyl)benzoate

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3 g of tert-butyl 4-(1-aminocyclopropyl)benzoate was placed in 30 mL of dichloromethane and 1.8 mL of pyridine. The solution was cooled to 0° C. and 1.2 mL of allyl chloroformate (dissolved in 5 mL of dichloromethane) was added dropwise at 0° C.-5° C. The mixture was left to react for 30 minutes at 0° C. and 2 hours at RT. The solution was combined with silica gel and evaporated down to the residue. This was chromatographed with dichloromethane on silica gel 70. Yield: 1.46 g of oil.

Workup

  1. waitThe mixture was left
  2. customto react for 30 minutes at 0° C. and 2 hours at RT
  3. customevaporated down to the residue
  4. customThis was chromatographed with dichloromethane on silica gel 70

Sources & evidence

ORD record
ord-6694c2a70f8044e589df03ded05a9648
Source dataset
uspto-grants-2010_05
Patent number
US07723381B2

Reaction notes

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