1,1-Dimethylhydrazine → HCID 18641471, compound

HRID 1088286Notes

Reaction equation

HRID 1088286 reaction equation
[N+:1]([C:4]1[CH:29]=[CH:28][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@H:15]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH2:14][C@H:13]2[CH2:25][CH:26]=O)=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:30][N:31]([CH3:33])[NH2:32].C(OCC)(=O)C>C(O)C>[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]([O:17][Si:18]([C:21]([CH3:23])([CH3:22])[CH3:24])([CH3:19])[CH3:20])[CH2:14][C@H:13]2[CH2:25][CH2:26][NH:32][N:31]([CH3:33])[CH3:30])=[O:11])=[CH:28][CH:29]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 59761,1-DimethylhydrazineHCID 8857Ethyl AcetateHCID 15671508HCID 15671508, compound

Product 1

HCID 18641471HCID 18641471, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(2S,4R)-1-p-Nitrobenzyloxycarbonyl-2-formylmethyl-4-t-butyldimethylsilyloxypyrrolidine (423 mg) was dissolved in 2 ml of ethanol, and 65 mg of N,N-dimethylhydrazine was added thereto, followed by stirring at room temperature for 15 minutes. To the reaction mixture was added ethyl acetate, and the mixture was washed with water, dried over anhydrous sodium sulfate and distilled to remove the solvent. The residue was purified by silica gel thin layer chromatography to obtain (2R,4R)-1-p-nitrobenzyloxycarbonyl-2-(2-dimethylhydrazinoethyl)-4-t-butyldimethylsilyloxypyrrolidine.

Workup

  1. washthe mixture was washed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. distillationdistilled
  4. customto remove the solvent
  5. customThe residue was purified by silica gel thin layer chromatography

Sources & evidence

ORD record
ord-2881b67e5c13454492e617f0a2e1d0de
Source dataset
uspto-grants-1990_10
Patent number
US04962103

Reaction notes

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