3-Pyridinemethanol → HCID 90203859, compound

HRID 927051Notes

Reaction equation

HRID 927051 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][C:8]1[C:9]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)=[N:10][O:11][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].[N:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27]O)[CH:22]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:1]([O:5][C:6](=[O:20])[NH:7][C:8]1[C:9]([C:13]2[CH:14]=[CH:15][C:16]([O:19][CH2:27][C:23]3[CH:22]=[N:21][CH:26]=[CH:25][CH:24]=3)=[CH:17][CH:18]=2)=[N:10][O:11][CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 75103-PyridinemethanolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 136491270HCID 136491270, compound

Product 1

HCID 90203859HCID 90203859, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [3-(4-hydroxy-phenyl)-isoxazol-4-yl]-carbamic acid tert-butyl ester (100 mg, 0.362 mmol), 3-pyridylmethanol (40 μL, 0.42 mmol)) and triphenylphosphine (200 mg, 0.76 mmol) in THF (2.1 mL) at 0° C. was added diethylazodicarboxylate (155 μL, 0.85 mmol) over 1.5 h. The reaction mixture was warmed rt for 24 h. Volatiles were removed under reduced pressure and the crude product was dry-loaded onto silica gel. Chromatography (1-2.5% CH3OH in CH2Cl2) provided {3-[4-(pyridin-3-ylmethoxy)-phenyl]isoxazol-4-yl}-carbamic acid tert-butyl ester.

Workup

  1. customVolatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-227ae88d118544d699d6efeb62581403
Source dataset
uspto-grants-2016_03
Patent number
US09290465B2

Reaction notes

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