Triphenylphosphine → HCID 10836736, compound

HRID 743237Notes

Reaction equation

HRID 743237 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[OH:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH:26]1[CH2:31][CH2:32]O)=[O:24])([CH3:21])([CH3:20])[CH3:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C(Cl)Cl>[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH:26]1[CH2:31][CH2:32][O:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[CH2:10][CH2:9][CH2:8][CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[O:24])([CH3:21])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 5103438Tert-butyl 2-(2-hydroxyethyl)piperidine-1-carboxylateHCID 125964892-(4-Phenylbutyl)phenol

Product 1

HCID 10836736HCID 10836736, compoundYield 34.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following a procedure similar to that described in Example 5(a), 1.69 g of 2-(4-phenylbutyl)phenol (prepared as described in Preparation 3), 1.72 g of 1-t-butoxycarbonyl-2-(2-hydroxyethyl)piperidine, 5.9 g of triphenylphosphine and 3.92 g of diethyl azodicarboxylate were reacted in 75 ml of methylene chloride. The crude oily product, extracted as described in Example 5(a), was purified by column chromatography through silica gel, using a 5:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 1.13 g (yield 34%) of the title compound as an oil.

Workup

  1. extractionThe crude oily product, extracted
  2. customwas purified by column chromatography through silica gel
  3. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-4079b2cba14c4eff88d617befb2759a7
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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