Triphenylphosphine → 7-((tetrahydro-2H-pyran-2-yloxy)methyl)-3,4-dihydro-2H-pyrano(3,2-c)pyridine

HRID 385602

Reaction equation

HRID 385602 reaction equation
O[CH2:2][CH2:3][CH2:4][C:5]1[C:6](=[O:19])[CH:7]=[C:8]([CH2:11][O:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][O:14]2)[NH:9][CH:10]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.C1(C)C=CC=CC=1>O1CCCC1>[O:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH:13]1[O:12][CH2:11][C:8]1[N:9]=[CH:10][C:5]2[CH2:4][CH2:3][CH2:2][O:19][C:6]=2[CH:7]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 578154885-(3-hydroxypropyl)-2-((tetrahydro-2H-pyran-2-yloxy)methyl)pyridin-4(1H)-oneHCID 66777355Diethylazodicarboxylate toluene

Product 1

HCID 578152547-((tetrahydro-2H-pyran-2-yloxy)methyl)-3,4-dihydro-2H-pyrano(3,2-c)pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.42 g of 5-(3-hydroxypropyl)-2-((tetrahydro-2H-pyran-2-yloxy)methyl)pyridin-4(1H)-one in 8 mL of tetrahydrofuran, 0.54 g of triphenylphosphine and 0.89 g of a 40% diethyl azodicarboxylate/toluene solution were added, and the mixture was stirred for 10 minutes. The solvent was distilled off under reduced pressure to obtain 7-((tetrahydro-2H-pyran-2-yloxy)methyl)-3,4-dihydro-2H-pyrano(3,2-c)pyridine as a brown oily substance.

Workup

  1. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-a72605121cb845608df0eb8c43357232
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Linked notes

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