Triphenylphosphine → HCID 18542735, compound

HRID 1268232Notes

Reaction equation

HRID 1268232 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:17]=[C:18](O)[C:19](=[CH:24][C:25]=1[N+:26]([O-:28])=[O:27])[C:20]([O:22][CH3:23])=[O:21].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:18]2[C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:24][C:25]([N+:26]([O-:28])=[O:27])=[C:16]([CH3:15])[CH:17]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 18542712HCID 18542712, compound

Product 1

HCID 18542735HCID 18542735, compoundYield 93.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-t-butoxycarbonyl-4-hydroxypiperidine (5.4 g), methyl 4-methyl-5-nitrosalicylate (2.8 g) and triphenylphosphine (9.0 g) in dichloromethane (100 ml) was added diethyl azodicarboxylate (5.4 ml) and the mixture was stirred at room temperature for 9 hours. The reaction mixture was concentrated in vacuo. The residue was purified by chromatography on a silica gel column using hexane/ethyl acetate=4/1 as an eluant to give the desired compound (4.9 g, yield 93%) as a yellow oil.

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-ab45f4ba28eb444088ddc074c5c376e7
Source dataset
uspto-grants-2003_04
Patent number
US06555556B1

Reaction notes

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