3-Hydroxypyridine → HCID 10636318, compound

HRID 617294Notes

Reaction equation

HRID 617294 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[C:32]([O:36][C:37]([N:39]1[CH2:43][CH2:42][CH2:41][C@H:40]1[CH2:44][OH:45])=[O:38])([CH3:35])([CH3:34])[CH3:33].O[C:47]1[CH:48]=[N:49][CH:50]=[CH:51][CH:52]=1>O1CCCC1>[C:32]([O:36][C:37]([N:39]1[CH2:43][CH2:42][CH2:41][C@H:40]1[CH2:44][O:45][C:47]1[CH:48]=[N:49][CH:50]=[CH:51][CH:52]=1)=[O:38])([CH3:35])([CH3:34])[CH3:33]

Participants

6

Reactant 4

HCID 79713-HydroxypyridineHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 643448(S)-(-)-N-Boc-prolinol

Product 1

HCID 10636318HCID 10636318, compoundYield 143.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of triphenylphosphine (1.97 g, 7.5 mmol) in 30 mL of tetrahydrofuran at room temperature was added diethyl azodicarboxylate (DEAD) (1.13 mL, 7.5 mmol) dropwise with stirring. After stirring at room temperature for 30 minutes, (S)-1-t-butoxycarbonyl-2-pyrrolidinemethanol (from Example 15a below, 1 g, 5.0 mmol) and 3-hydroxypyridine (713 mg, 7.5 mmol) were added to the reaction mixture. The resultant solution was stirred at room temperature for 16 hr. After all the starting material was consumed, the organic solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography. Elution with chloroform:methanol (10:1) provided 2 g of the title compound. MS (DCI/NH3) m/e 279 (M+H)+.

Workup

  1. stirringAfter stirring at room temperature for 30 minutes
  2. customAfter all the starting material was consumed
  3. customthe organic solvent was evaporated in vacuo
  4. customThe residue was purified by silica gel column chromatography
  5. washElution with chloroform:methanol (10:1)

Sources & evidence

ORD record
ord-250746a4e28c42f0834b26223e8ed39d
Source dataset
uspto-grants-1999_09
Patent number
US05948793

Reaction notes

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