Triphenylphosphine → 1-t-Butoxycarbonyl-4-{2-[2-(3-methoxyphenyl)ethyl]phenoxy}piperidine

HRID 743248Notes

Reaction equation

HRID 743248 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[OH:17])[CH:6]=[CH:7][CH:8]=1.[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][CH:28](O)[CH2:27][CH2:26]1)=[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][CH:28]([O:17][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH2:10][CH2:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:19])[CH3:20]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 105854482-(2-(3-Methoxyphenyl)ethyl)phenol

Product 1

HCID 106215801-t-Butoxycarbonyl-4-{2-[2-(3-methoxyphenyl)ethyl]phenoxy}piperidineYield 46.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following a procedure similar to that described in Example 36(a), 456 mg of 2-[2-(3-methoxyphenyl)ethyl]phenol (prepared as described in Preparation 20), 600 mg of 1-t-butoxycarbonyl-4-hydroxypiperidine and 865 mg of triphenylphosphine were reacted with 575 mg of diethyl azodicarboxylate in 30 ml of methylene chloride. The reaction mixture was worked up as described in Example 6(a), and the crude product thus obtained was purified by column chromatography through silica gel, using a 4:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 379 mg (yield 46%) of the title compound as a colorless oil.

Workup

  1. customthe crude product thus obtained
  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-1303aeef297843a5b56dade2eb43b220
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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