Triphenylphosphine → 1-Boc-4-(2-pyridyloxy)piperidine

HRID 1246754Notes

Reaction equation

HRID 1246754 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.O[CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[O:1][CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 178516071HCID 178516071, compound

Product 1

HCID 219060391-Boc-4-(2-pyridyloxy)piperidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-hydroxypyridine (2.0 g), tert-butyl 4-hydroxy-1-piperidinecarboxylate (5.3 g) and triphenylphosphine (8.3 g) in tetrahydrofuran (63 ml) was slowly added diethyl azodicarboxylate (5.5 g) at 8° C., and the mixture was stirred at room temperature for 4 hours. The reaction mixture was concentrated in vacuo to give the crude product of the title compound and the crude product was purified by chromatography on silica gel.

Workup

  1. customat 8° C.
  2. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-c8d9c4749fb54a3599bbfd5cec6c6a38
Source dataset
uspto-grants-2006_10
Patent number
US07129243B2

Reaction notes

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