tert-Butanol → HCID 86615516、化合物

HRID 1158768ノート

反応式

HRID 1158768 の反応式
C=C1C[O:6][C@H:5]([C:8]2[CH:13]=[C:12]([F:14])[C:11]([F:15])=[CH:10][C:9]=2[F:16])[C@@H:4]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])C1.C[N+]1([O-])CC[O:29]CC1.S(=O)(O)[O-].[Na+].C(OCC)(=O)C.[C:44]([OH:48])([CH3:47])([CH3:46])[CH3:45]>CC(C)=O.O.[Os](=O)(=O)(=O)=O>[OH:48][C:44]1([CH2:47][OH:29])[CH2:46][O:6][C@H:5]([C:8]2[CH:13]=[C:12]([F:14])[C:11]([F:15])=[CH:10][C:9]=2[F:16])[C@@H:4]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:45]1

参加物

9

反応物 5

HCID 6386tert-ButanolHCID 8857Ethyl AcetateHCID 82029Methyl morpholine oxideHCID 23665763Sodium BisulfiteHCID 86615515HCID 86615515、化合物

生成物 1

HCID 86615516HCID 86615516、化合物

試薬・触媒・溶媒 3

HCID 30318Osmium Tetroxide触媒HCID 180Acetone溶媒HCID 962Water溶媒

実験手順

To a solution of tert-butyl [(2R,3S)-5-methylene-2-(2,4,5-trifluorophenyl)tetrahydro-2H-pyran-3-yl]carbamate (203 mg, 0.59 μmmol) in tert-butyl alcohol (6 mL), acetone (3 mL) and water (1.5 mL) was added osmium tetroxide (0.113 mL of 2.5% solution in tert-butyl alcohol, 0.009 mmol). The resultant mixture was stirred at room temperature for 10 minutes and then treated with N-methylmorpholine N-oxide (92 mg, 0.79 mmol) and stirred for two days. After two days, the reaction mixture was treated with aqueous sodium bisulfite solution (5 mL, 2.0N) followed after 10 min by ethyl acetate. The organic layer was washed successively with 2N hydrochloric acid and saturated aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate, filtered and evaporated to yield tert-butyl [(2R,3S)-5-hydroxy-5-(hydroxymethyl)-2-(2,4,5-trifluorophenyl)tetrahydro-2H-pyran-3-yl]carbamate which was used in the next step without further purification.

後処理

  1. waitAfter two days
  2. washThe organic layer was washed successively with 2N hydrochloric acid and saturated aqueous sodium bicarbonate solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated

出典と根拠

ORDレコード
ord-d7656aa1b6694acab43a784c4b84cd4d
出典データセット
uspto-grants-2010_10
特許番号
US07812027B2

反応ノート

読み込み中…