Triphenylphosphine → HCID 22181030, compound

HRID 1268196Notes

Reaction equation

HRID 1268196 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].[N+:15]([C:18]1[CH:28]=[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:21](O)=[CH:20][CH:19]=1)([O-:17])=[O:16].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>ClCCl.CCCCCC>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:21]2[CH:20]=[CH:19][C:18]([N+:15]([O-:17])=[O:16])=[CH:28][C:22]=2[C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 12512105HCID 12512105, compound

Product 1

HCID 22181030HCID 22181030, compoundYield 61.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

To a solution of 1-t-butoxycarbonyl-4-hydroxypiperidine (10.2 g), ethyl 5-nitrosalicylate (10.7 g) and triphenylphosphine (17.3 g) in dichloromethane (200 ml) was added dropwise diethyl azodicarboxylate (10.4 ml) in an ice bath 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=3/1 as an eluant to afford a yellow solid. A suspension of the solid in hexane was filtered to give the desired compound (12.3 g, yield 61%) 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. filtrationwas filtered

Sources & evidence

ORD record
ord-87a3d0f5050344ea8757f1382bdc7303
Source dataset
uspto-grants-2003_04
Patent number
US06555556B1

Reaction notes

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