Triethylamine → Benzyl cyclopropylcarbamate

HRID 2361882Notes

Reaction equation

HRID 2361882 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.C(N(CC)CC)C.Cl[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14]>ClCCl>[CH2:16]([O:15][C:13](=[O:14])[NH:4][CH:1]1[CH2:3][CH2:2]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformate2×HCID 69828Cyclopropylamine

Product 1

HCID 13141013Benzyl cyclopropylcarbamateYield 587.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of cyclopropylamine (5.0 g, 87.5 mmol) and triethylamine (30 mL) in dichloromethane (100 mL) at 0° C. was added dropwise benzyl chloroformate (15.0 mL, 10.5 mmol) and the resulting mixture was stirred for 2 h. Additional benzyl chloroformate (1 mL) was added and the resulting reaction mixture was stirred overnight. The reaction was then quenched by addition of a saturated NaHCO3 and the separated aqueous phase was extracted several times with dichloromethane. The combined dichloromethane extracts were dried over Na2SO4, filtered and concentrated. The residue was purified by chromatography (15% EtOAc to 5% MeOH/EtOAc) to give cyclopropyl-carbamic acid benzyl ester (11.8 g, 71%).

Workup

  1. customthe resulting reaction mixture
  2. stirringwas stirred overnight
  3. customThe reaction was then quenched by addition of a saturated NaHCO3
  4. extractionthe separated aqueous phase was extracted several times with dichloromethane
  5. dry with materialThe combined dichloromethane extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography (15% EtOAc to 5% MeOH/EtOAc)

Sources & evidence

ORD record
ord-778c4d04b31f4483a8ece20ab30996a3
Source dataset
uspto-grants-2014_04
Patent number
US08691814B2

Reaction notes

Loading…