Triphenylphosphine → HCID 18542692, compound

HRID 1268225Notes

Reaction equation

HRID 1268225 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:15][C:16]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[C:18]([CH3:25])[C:17]=1O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:17]2[C:18]([CH3:25])=[CH:19][C:20]([N+:22]([O-:24])=[O:23])=[CH:21][C:16]=2[CH3:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 170302,6-Xylenol, 4-nitro-HCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 18542692HCID 18542692, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-t-butoxycarbonyl-4-hydroxypiperidine (2.40 g), 2,6-dimethyl-4-nitrophenol (1.50 g) and triphenylphosphine (3.06 g) in dichloromethane (60 ml) was added dropwise diethyl azodicarboxylate (1.80 ml) in an ice bath and the mixture was stirred at room temperature for 19 hours. The reaction mixture was concentrated in vacuo. The residue was purified by chromatography on a silica gel column using hexane/ethyl acetate=5/1 as an eluant to give the desired compound (2.25 g, yield 71%) as a colorless solid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-6aad36520e174e52a1b1d25f2a560e00
Source dataset
uspto-grants-2003_04
Patent number
US06555556B1

Reaction notes

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