Nitromethane → HCID 10644137, compound

HRID 1755765Notes

Reaction equation

HRID 1755765 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 15 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-2nitroethyl)pyrrolidine (14.81 g, yield: 65.5%).

Workup

  1. temperaturecooling with ice
  2. waitThis solution was left
  3. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-70bd6fc651d14e219509d23ee78255ab
Source dataset
uspto-grants-1995_08
Patent number
US05438054

Reaction notes

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