HCID 19094442, compound → HCID 14986548, compound

HRID 487211Notes

Reaction equation

HRID 487211 reaction equation
C([O:8][N:9]1[CH2:13][CH2:12][C:11]2([C:18]3[CH:19]=[C:20]([F:23])[CH:21]=[CH:22][C:17]=3[O:16][CH2:15][CH2:14]2)[C:10]1=[O:24])C1C=CC=CC=1>CO.[Pd]>[OH:8][N:9]1[CH2:13][CH2:12][C:11]2([C:18]3[CH:19]=[C:20]([F:23])[CH:21]=[CH:22][C:17]=3[O:16][CH2:15][CH2:14]2)[C:10]1=[O:24]

Participants

4

Reactant 1

HCID 19094442HCID 19094442, compound

Product 1

HCID 14986548HCID 14986548, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

A solution of 1'-benzyloxy-2,3-dihydro-6-fluorospiro-(4H-1-benzopyran-4,3'-pyrrolidine)-2'-one (1.4 g) in methanol (75 mL) containing 10% palladium on carbon (300 mg) was stirred vigorously under hydrogen gas (1 atm). After 18 hours, more palladium on carbon (300 mg) was added, and the mixture was then filtered after being stirred under hydrogen gas for a further 20 minutes. The filtrate was concentrated in vacuo, and the residue purified by silica gel chromatography, eluting with ethyl acetate, to afford the title compound as a white crystalline solid, 780 mg, m.p. 208°-209° C.

Workup

  1. filtrationthe mixture was then filtered
  2. stirringafter being stirred under hydrogen gas for a further 20 minutes
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue purified by silica gel chromatography
  5. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-a7ca173b4e33464a82591056ef512ea4
Source dataset
uspto-grants-1994_03
Patent number
US05294635

Reaction notes

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