Nitromethane → HCID 69686501, compound

HRID 1936629Notes

Reaction equation

[C:1]([O:5][C:6]([C@H:8]1[CH2:10][C@@H:9]1[CH:11]=[CH:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:18]N(C)C(=N)N(C)C.[N+:26]([CH3:29])([O-:28])=[O:27]>>[C:1]([O:5][C:6]([C@H:8]1[CH2:10][C@@H:9]1[CH:11]([CH2:18][CH2:29][N+:26]([O-:28])=[O:27])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 3

HCID 6375Nitromethane

HCID 664601,1,3,3-Tetramethylguanidine

HCID 69686662HCID 69686662, compound

Product 1

HCID 69686501HCID 69686501, compoundYield 87.2%

Conditions

Temperature: 70 °C

Procedure

To 150 ml of a nitromethane solution of 17.33 g (72.1 mmol) of ethyl 3-[(1R,2S)-2-t-butoxycarbonylcyclopropyl)acrylate was added 14.47 ml (115.4 mmol) of tetramethylguanidine at room temperature, and the mixture was stirred at 70° C. for 3.5 hours. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=85:15) to give 18.95 g (87.2%) of the title compound as a colorless oily substance.

Workup

customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=85:15)

Sources & evidence

ORD record: ord-4fd70461ab3946b5872862e7e96dcb7c
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06391889B1

Reaction notes

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