Hydrazine hydrate (1:1) → (2S,4S)-2-aminomethyl-1-(4-nitrobenzyloxycarbonyl)-4-(triphenylmethylthio)pyrrolidine

HRID 1034481Notes

Reaction equation

HRID 1034481 reaction equation
[N+:1]([C:4]1[CH:50]=[CH:49][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@@H:15]([S:17][C:18]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:14][C@H:13]2[CH2:37][N:38]2C(=O)C3=CC=CC=C3C2=O)=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].O.NN>ClCCl.CO>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@@H:15]([S:17][C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:14][C@H:13]2[CH2:37][NH2:38])=[O:11])=[CH:49][CH:50]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 57302820(2s,4s)-1-p-Nitrobenzyloxycarbonyl-2-phthalimidomethyl-4-tritylthiopyrrolidine

Product 1

HCID 15056148(2S,4S)-2-aminomethyl-1-(4-nitrobenzyloxycarbonyl)-4-(triphenylmethylthio)pyrrolidineYield 91%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,4S)-1-p-nitrobenzyloxycarbonyl-2-phthalimidomethyl-4-tritylthiopyrrolidine (10.46 g: 15.31 mmole) in a mixture of dichloromethane (80 ml) and methanol (160 ml), hydrazine hydrate (1.53 ml: 2 eq.) is added, and the mixture is concentrated to remove dichloromethane by warming and refluxed for 3 hours and 15 minutes. The reaction mixture is concentrated in vacuo. The residue is diluted with dichloromethane and filtered to remove solid. The filtrate is washed with water, dried over magnesium sulfate, and concentrated in vacuo to give crude (2S,4S)-1-p-nitrobenzyloxycarbonyl-2-aminomethyl-4-tritylthiopyrrolidine (7.71 g). Yield: 91%. NMR δ(CDCl3 :CD3OD=2:1) ppm: 1.46 to 3.76(m, 10H), 5.04, 5.12(ABq, J=15 Hz, 2H), 7.10 to 7.56(m, 17H), 8.12 to 8.30(m, 2H). IR ν (CHCl3) cm-1 : 1695, 1606.

Workup

  1. additionis added
  2. concentrationthe mixture is concentrated
  3. customto remove dichloromethane
  4. temperatureby warming
  5. temperaturerefluxed for 3 hours and 15 minutes
  6. concentrationThe reaction mixture is concentrated in vacuo
  7. additionThe residue is diluted with dichloromethane
  8. filtrationfiltered
  9. customto remove solid
  10. washThe filtrate is washed with water
  11. dry with materialdried over magnesium sulfate
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-20e9d589e6964e5aa9dc30ab53058dd0
Source dataset
uspto-grants-1994_05
Patent number
US05317016

Reaction notes

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