HCID 19094442, compound → HCID 14986548, compound

HRID 2248290Notes

Reaction equation

HRID 2248290 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-fluoro-spiro-(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-9d5b77af8c284ddf8fb8c342dbb9e502
Source dataset
uspto-grants-1991_08
Patent number
US05039672

Reaction notes

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