Ammonium Chloride → HCID 78035270, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl 2-((1SR,2SR)-2-(methoxycarbonylamino)-2-(3-nitrophenyl)cyclopropyl)acetate (intermediate B10a) (2.45 g, 7.6 mmol, Eq: 1.00) was dissolved in tetrahydrofuran (80 ml) and lithium borohydride (2 M in THF; 8.36 ml, 16.7 mmol, Eq: 2.2) was added dropwise at 5° C. The turbid solution was stirred at 23° C. for 6 hours. The reaction mixture was poured into ice water, sat NH4Cl solution (100 ml) was added slowly and the mixture was stirred vigorously for 45 min (gas evolution finished). Then extraction with EtOAc, the organic layer was dried over Na2SO4, filtration and evaporation of the solvent left a yellow oil (2.5 g; 117%). Crystallization with dichloromethane/cyclohexane gives the methyl (1SR,2SR)-2-(2-hydroxyethyl)-1-(3-nitrophenyl)cyclopropylcarbamate (1.84 g, 6.56 mmol, 86.4% yield) as a light yellow solid. MS (ISP): m/z=281.1 [(M+H)+].

Provenance & Evidence