3-Hydroxypyridine → HCID 21906079, compound

HRID 1168991Notes

Reaction equation

HRID 1168991 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[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 79713-HydroxypyridineHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 21906079HCID 21906079, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, a cold (0-5° C.), stirring solution of N-(tert-butoxycarbonyl)-piperidin-4-ol (800 mg, 3.98 mmol), 3-hydroxypyridine (378 mg, 3.98 mmol) and triphenylphosphine (1.148 g, 4.38 mmol) in dry tetrahydrofuran (20 mL) was treated drop-wise via syringe with diethyl azodicarboxylate (0.75 mL, 830 mg, 4.76 mmol). The mixture was allowed to stir and warm to ambient temperature over 16 h. The solvent was removed by rotary evaporation, and the crude product was purified by column chromatography over silica gel, eluting with hexane-ethyl acetate-(9:1, v/v). Selected fractions were collected and concentrated to produce 800 mg (72%) of a thick syrup.

Workup

  1. customThe solvent was removed by rotary evaporation
  2. customthe crude product was purified by column chromatography over silica gel
  3. washeluting with hexane-ethyl acetate-(9:1
  4. customSelected fractions were collected
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cac913d29a404b7baef85cc16803bf67
Source dataset
uspto-grants-2003_09
Patent number
US06627648B1

Reaction notes

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