Triphenylphosphine → HCID 18542737, compound

HRID 1268213Notes

Reaction equation

HRID 1268213 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].[Cl:15][C:16]1[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[C:18]([C:19]([O:21][CH3:22])=[O:20])[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]([C:19]([O:21][CH3:22])=[O:20])=[CH:23][C:24]([N+:26]([O-:28])=[O:27])=[CH:25][C:16]=2[Cl:15])[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 18542715HCID 18542715, compound

Product 1

HCID 18542737HCID 18542737, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-t-butoxycarbonyl-4-hydroxypiperidine (6.3 9), methyl 3-chloro-5-nitrosalicylate (2.4 g) and triphenylphosphine (10.8 g) in dichloromethane (100 ml) was added diethyl azodicarboxylate (6.6 ml) and the mixture was stirred at room temperature for 4 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 (3.4 g, yield 79%) as a pink 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-6fdd6729002c4f8f8e3217b43084e58d
Source dataset
uspto-grants-2003_04
Patent number
US06555556B1

Reaction notes

Loading…