(+)-8-Phenylmenthol → HCID 69303668、化合物

HRID 635977

反応式

HRID 635977 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:14]3[S:15](=[O:19])(=[O:18])[CH2:16][CH2:17][C:13]=3[NH:12][C:11]3[CH2:20][O:21][CH2:22][C:23](=[O:24])[C:10]2=3)[CH:5]=[CH:6][C:7]=1[F:8].CC(C)([O-])C.[K+].Cl[C:32]([O:34][CH:35]1[CH:40]([C:41]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)([CH3:43])[CH3:42])[CH2:39][CH2:38][CH:37]([CH3:50])[CH2:36]1)=[O:33].C1(C(C)(C)C2CCC(C)CC2O)C=CC=CC=1>C1COCC1.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:14]3[S:15](=[O:18])(=[O:19])[CH2:16][CH2:17][C:13]=3[N:12]([C:32]([O:34][C@@H:35]3[CH2:36][C@H:37]([CH3:50])[CH2:38][CH2:39][C@H:40]3[C:41]([CH3:42])([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[CH3:43])=[O:33])[C:11]3[CH2:20][O:21][CH2:22][C:23](=[O:24])[C:10]2=3)[CH:5]=[CH:6][C:7]=1[F:8]

参加物

7

反応物 4

HCID 577105(+)-8-PhenylmentholHCID 9887983(+)-9-(3-Bromo-4-fluorophenyl)-2,3,5,9-tetrahydro-4h-pyrano[3,4-b]thieno[2,3-e]pyridin-8(7h)-one 1,1-dioxideHCID 145714908-Phenylmenthol chloroformateHCID 23665647Potassium tert-butoxide

生成物 1

HCID 69303668HCID 69303668、化合物

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒3 回

実験手順

To a suspension of the product from Example 11D (1.58 g, 3.7 mmol) in THF (40 mL) at 0° C. under a nitrogen atmosphere was added a 1M solution of potassium tert-butoxide in THF (4.1 mL) dropwise over 5 minutes. The mixture was stirred at ambient temperature for 30 minutes, cooled to 0° C., treated with a solution of 8-phenylmenthol chloroformate prepared from (−)-8-phenylmenthol as described in (Yamamoto, Y., J. Amer. Chem. Soc. (1992), 114, 121-125) (1.31 g, 4.4 mmol) in THF (20 mL) over 5 minutes, stirred at ambient temperature for 16 hours, diluted with methylene chloride (150 mL) and washed with aqueous sodium bicarbonate (30 mL). The layers were separated and the aqueous layer was extracted with methylene chloride (50 mL). The combined organic layers were dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography over silica gel (3:2:1 chloroform/hexanes/diethyl ether) to provide 0.98 g of the less polar diasteriomer.

後処理

  1. temperaturecooled to 0° C.
  2. stirringstirred at ambient temperature for 16 hours
  3. washwashed with aqueous sodium bicarbonate (30 mL)
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with methylene chloride (50 mL)
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography over silica gel (3:2:1 chloroform/hexanes/diethyl ether)
  10. customto provide 0.98 g of the less polar diasteriomer

出典と根拠

ORDレコード
ord-73265167ee1d421db5dd781435b3ae12
出典データセット
uspto-grants-2001_02
特許番号
US06191140B1

関連ノート

読み込み中…