HCID 66803796, compound → HCID 66803947, compound

HRID 2190994Notes

Reaction equation

HRID 2190994 reaction equation
[CH2:1]([C:3]1[CH2:4][CH:5]2[CH:8]([CH:9]=1)[C:7]([CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])([CH2:10][N+:11]([O-])=O)[CH2:6]2)[CH3:2].[H][H]>[Ni].C(O)C>[NH2:11][CH2:10][C:7]1([CH2:14][C:15]([O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:16])[CH2:6][CH:5]2[CH:8]1[CH:9]=[C:3]([CH2:1][CH3:2])[CH2:4]2

Participants

5

Reactant 2

HCID 66803796HCID 66803796, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66803947HCID 66803947, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

Raney nickel (96 mg, 0.16 w/w) and ethanol (200 μL) were added to tert-butyl [3-ethyl-6-(nitromethyl)bicyclo[3.2.0]hept-3-en-6-yl]acetate (59 mg, 85:15 diastereomeric mixture), and the mixture was stirred at room temperature for 12 hours under the hydrogen atmosphere. The Raney nickel was filtered off. Then, the solvent was distilled off to obtain the compound of interest as a brown oil substance (49 mg, yield: 92%, 85:15 diastereomeric mixture).

Workup

  1. filtrationThe Raney nickel was filtered off
  2. distillationThen, the solvent was distilled off
  3. customto obtain the compound of interest as a brown oil substance (49 mg, yield: 92%, 85:15 diastereomeric mixture)

Sources & evidence

ORD record
ord-71d94fec3c1f43c8acbcba92c9dc36b5
Source dataset
uspto-grants-2012_12
Patent number
US08324425B2

Reaction notes

Loading…