Hydrazine hydrate (1:1) → HCID 69820370, compound

HRID 350519Notes

Reaction equation

HRID 350519 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([N:13]2C(=O)C3=CC=CC=C3C2=O)[CH2:10][C@H:9]1[CH2:24][O:25][Si:26]([C:39]([CH3:42])([CH3:41])[CH3:40])([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].NN.O>CCO>[NH2:13][C@@H:11]1[CH2:12][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[C@H:9]([CH2:24][O:25][Si:26]([C:39]([CH3:42])([CH3:41])[CH3:40])([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:10]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 69332180HCID 69332180, compound

Product 1

HCID 69820370HCID 69820370, compoundYield 104.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of N-[cis-1tert-butoxycarbonyl-(2S)-(tert-butyldiphenylsilyloxy) methyl-4-pyrrolidinyl]phthalimide (1.60 g, 2.74 mmol) in EtOH (8 ml) was added NH2NH2.H2O(206 mg, 4.11 mmol) at room temperature. The reaction mixture was stirred at 70 for 1 hr. The mixture was concentrated in vacuo. The resulting solid was filtered off, and washed with CHCl3. The filtrate was concentrated in vacuo. The resulting solid was filtered off, and washed with CHCl3. The filtrate was concentrated in vacuo to give cis-4-amino-1-tert-butoxycarbonyl-(2S)-(tert-butyl diphenylsilyloxy) methylpyrrolidine (1.3 g, quant) as a pale yellow oil. The crude product was used to the subsequent reaction without further purification. 1H-NMR (CDCl3) δ 1.06 (s, 9H), 1.30 and 1.45 (each s, total 91), 1.59 (m, 1H), 1.85 (m, 1H), 2.94 (m, 1H), 3.44 (m, 1H), 3.78–4.07 (m, 4H), 7.36–7.41 (m, 6H), 7.51–7.65 (m, 4H).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. filtrationThe resulting solid was filtered off
  3. washwashed with CHCl3
  4. concentrationThe filtrate was concentrated in vacuo
  5. filtrationThe resulting solid was filtered off
  6. washwashed with CHCl3
  7. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-5150595d9da042b4aabe067115636dc5
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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