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

HRID 743270Notes

Reaction equation

HRID 743270 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][CH2:28][CH:27](O)[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:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][CH2:28][CH:27]([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)[CH2:26]1)=[O:24])([CH3:21])([CH3:19])[CH3:20]

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 5456991-Boc-3-hydroxypiperidineHCID 105854482-(2-(3-Methoxyphenyl)ethyl)phenol

Product 1

HCID 105017801-t-Butoxycarbonyl-3-{2-[2-(3-methoxyphenyl)ethyl]phenoxy}piperidineYield 62.1%

Procedure

Following a procedure similar to that described in Example 36(a), 1.50 g of 2-[2-(3-methoxyphenyl)ethyl]phenol (prepared as described in Preparation 20), 2.64 g of 1-t-butoxycarbonyl-3-hydroxypiperidine, 3.44 g of triphenylphosphine and 2.29 g of diethyl azodicarboxylate were reacted. The mixture was then worked up as described in Example 36(a), and the crude product thus obtained was purified by column chromatography through silica gel, using a 7:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 1.68 g (yield 62%) of the title compound as a colorless oil.

Workup

  1. customwere reacted
  2. customthe crude product thus obtained
  3. customwas purified by column chromatography through silica gel
  4. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-676ed4a4f5a1435ca4619005e47e2159
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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