Nitromethane → HCID 10644137, compound

HRID 1492822Notes

Reaction equation

HRID 1492822 reaction equation
C(N(CC)CC)C.[O:8]([C@H:16]1[CH2:20][N:19]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@H:18]([CH:28]=[O:29])[CH2:17]1)[Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].[N+:30]([CH3:33])([O-:32])=[O:31]>>[O:8]([C@H:16]1[CH2:20][N:19]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@H:18]([CH:28]([OH:29])[CH2:33][N+:30]([O-:32])=[O:31])[CH2:17]1)[Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]

Participants

4

Reactant 3

HCID 6375NitromethaneHCID 8471TriethylamineHCID 10969557tert-Butyl (2S,4R)-4-((tert-butyldimethylsilyl)oxy)-2-formylpyrrolidine-1-carboxylate

Product 1

HCID 10644137HCID 10644137, compoundYield 65.5%

Procedure

Triethylamine (1.27 ml, 9.55 mmol) was added to a solution of (2S,4R)-4-tert-butyldimethylsiloxy-N-tert-butoxycarbonylprolinal (19.1 g, 57.87 mmol) in nitromethane (95 ml) under stirring and cooling with ice. This solution was left to stand at room temperature for hours. The solvent was distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography (Wakogel™ C-300, 350 g, hexane-ethyl acetate 9:1) to obtain oily (2S,4R)-4-tert-butyldimethylsiloxy-N-tert-butoxycarbonyl-2-(1-hydroxy-2-nitroethyl)pyrrolidine (14.81 g, yield: 65.5%). IR(KBr)cm-1 : 3420, 1675, 1700, 1560, 1415, 1255, 1165, 840, 780

Workup

  1. temperaturecooling with ice
  2. waitThis solution was left
  3. waitto stand at room temperature for hours
  4. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-cb9b7893a0ba4c09afca33e30e540163
Source dataset
uspto-grants-1994_12
Patent number
US05374720

Reaction notes

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