8-Allyl-1-ethyl-7-fluoro-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid methyl ester → 8-Allyl-1-ethyl-7-fluoro-4-oxo-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid methyl ester

HRID 399773Notes

Reaction equation

HRID 399773 reaction equation
[CH3:1][O:2][C:3](=[O:24])[CH2:4][C:5]1([CH2:22][CH3:23])[C:10]2[NH:11][C:12]3[C:17]([C:9]=2[CH2:8][CH2:7][O:6]1)=[CH:16][CH:15]=[C:14]([F:18])[C:13]=3[CH2:19][CH:20]=[CH2:21].CC1(C)N([O])C(C)(C)CCC1.F[B-](F)(F)F.CC#N.[OH2:44]>>[CH3:1][O:2][C:3](=[O:24])[CH2:4][C:5]1([CH2:22][CH3:23])[C:10]2[NH:11][C:12]3[C:17]([C:9]=2[C:8](=[O:44])[CH2:7][O:6]1)=[CH:16][CH:15]=[C:14]([F:18])[C:13]=3[CH2:19][CH:20]=[CH2:21]

Participants

4

Reactant 3

HCID 147700108-Allyl-1-ethyl-7-fluoro-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid methyl esterHCID 18373917Acetonitrile--water (1/1)2×HCID 178424956HCID 178424956, compound

Product 1

HCID 676190068-Allyl-1-ethyl-7-fluoro-4-oxo-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid methyl ester

Procedure

A solution of the ester (0.21 g, 0.63 mmol, prepared as described in Step A), in 10 ml of CH3CN--H2O(9:1, v/v) was added dropwise to a stirred solution of TEMPO-BF4 in 10 ml CH3CN--H2O (9:1, v/v). Stirring was continued for 2 h and the reaction mixture was concentrated in vacuo. The residue was partitioned between Et2O and H2O. The organic phase was washed with brine and dried (Na2 SO4). Removal of solvent provides a yellow oil which was purified by flash chromatography (silica gel, hexane-EtOAc 2:1) to give 0.18 g of product as an off white solid.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customThe residue was partitioned between Et2O and H2O
  3. washThe organic phase was washed with brine
  4. customdried (Na2 SO4)
  5. customRemoval of solvent
  6. customprovides a yellow oil which
  7. customwas purified by flash chromatography (silica gel, hexane-EtOAc 2:1)

Sources & evidence

ORD record
ord-a117d8f7d6864ca0a846c757d0387e41
Source dataset
uspto-grants-1998_10
Patent number
US05824699

Reaction notes

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