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 399773ノート

反応式

HRID 399773 の反応式
[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]

参加物

4

反応物 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 回HCID 178424956HCID 178424956、化合物

生成物 1

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

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-a117d8f7d6864ca0a846c757d0387e41
出典データセット
uspto-grants-1998_10
特許番号
US05824699

反応ノート

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