HCID 19820679, compound → HCID 57122995, compound

HRID 2249117Notes

Reaction equation

HRID 2249117 reaction equation
[CH2:1]([O:3][CH2:4][C:5]([CH2:24][O:25][CH2:26][CH3:27])([OH:23])[CH:6]([N+:20]([O-])=O)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:10][CH:9]=1)[CH3:2].[H][H]>[Ni].C(O)(C)C>[CH2:26]([O:25][CH2:24][C:5]([CH2:4][O:3][CH2:1][CH3:2])([OH:23])[CH:6]([NH2:20])[CH2:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:12][CH:13]=1)[CH3:27]

Participants

5

Reactant 2

HCID 19820679HCID 19820679, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57122995HCID 57122995, compoundYield 85.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 3776IsopropanolSolvent

Procedure

A mixture of α, α-diethoxymethyl-β-nitro-4-hexylbenzenepropanol (2.31 g) and Raney nickel (0.6 g) in isopropanol (70 ml) was stirred under hydrogen at atmospheric pressure until the hydrogen absorption was complete. The mixture was degased in vacuo for 15 minutes and filtered through celite. Evaporation of solvent gave α, α-diethoxymethyl-β-amino-4-hexylbenzenepropanol (1.82 g) as an oil. This oil was reacted with di-tert-butyl-dicarbonate (1.19 g) in methanol (40 ml). The mixture was stirred at room temperature for 2 hours. The solvent was evaporated and the residue was purified by chromatography [silica gel 290 g, elution with ethyl acetate: cyclohexane, 2:8 (2 1)]. Two isomers of the title compound were isolated. Isomer A (0.90 g) and isomer B (0.90 g) were obtained as oils, Rf isomer A=0.30, Rf isomer B=0.19 (silica gel, ethyl acetate: cyclohexane, 1:4)

Workup

  1. customThe mixture was degased in vacuo for 15 minutes
  2. filtrationfiltered through celite
  3. customEvaporation of solvent

Sources & evidence

ORD record
ord-67dd098344094763a91be610ffb4ab4d
Source dataset
uspto-grants-1991_08
Patent number
US05041673

Reaction notes

Loading…