Hydrazine hydrate (1:1) → HCID 10578323, compound

Participants

Reaction Steps

To a solution of (2S,4S)-1-p-methoxybenzyloxycarbonyl-2-phthalimidomethyl-4-tritylthiopyrrolidine (752 mg: 1.124 mmole) in a mixture of dichloromethane (3 ml) and methanol (12 ml), hydrazine hydrate (109 μl: 2 eq.) is added. The mixture is heated for 5 hours. The reaction mixture is concentrated in vacuo. The residue is dissolved in dichloromethane (5 ml) and the solid is filtered off. The filtrate is washed with water and concentrated in vacuo. The residue is recrystallized from a mixture of dichloromethane and methanol to give (2S,4S)-1-p-methoxybenzyloxycarbonyl-2-aminomethyl-4-tritylthiopyrrolidine (471 mg). Yield: 78%. mp. 165° to 167° C. NMR δ(CDCl3 :CD3OD=2:1) ppm: 3.46(s, 3H), 4.96, 4.89(ABq, J=12 Hz, 2H). IR ν (CHCl3) cm-1 : 1683, 1610.

Provenance & Evidence