Triphenylphosphine → HCID 18542632, compound

HRID 1268229Notes

Reaction equation

HRID 1268229 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].O[C:16]1[C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][C:23]([N+:30]([O-:32])=[O:31])=[CH:22][C:17]=1[C:18]([O:20][CH3:21])=[O:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>ClCCl.O1CCCC1.CCCCCC.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:16]2[C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:22][C:23]([N+:30]([O-:32])=[O:31])=[CH:24][C:25]=2[C:26]([O:28][CH3:29])=[O:27])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 139742081,3-Benzenedicarboxylic acid, 2-hydroxy-5-nitro-, 1,3-dimethyl ester

Product 1

HCID 18542632HCID 18542632, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a solution of 1-t-butoxycarbonyl-4-hydroxypiperidine (2.6 g), dimethyl 2-hydroxy-5-nitroisophthalate (1.6 g) and triphenylphosphine (4.4 g) in a mixture of dichloromethane (40 ml) and tetrahydrofuran (20 ml) was added diethyl azodicarboxylate (2.6 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 dichloromethane/ethyl acetate=19/1 as an eluant to afford a yellow solid. To the solid was added hexane/ethyl acetate=4/1 and then the mixture was filtered to give the desired compound (2.2 g, yield 78%) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe residue was purified by chromatography on a silica gel column
  3. customto afford a yellow solid
  4. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-4d4df02c10ba4cc3a30f2d8528dd7114
Source dataset
uspto-grants-2003_04
Patent number
US06555556B1

Reaction notes

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