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Ethyl Acetate → 2-(trimethylsilyl)ethyl rac-[(1R,2S,3R)-2,3-dihydroxy-1-methyl-2,3-dihydro-1H-inden-1-yl]carbamate

HRID 64454
ノート
印刷プレビュー

反応式

HRID 64454 の反応式
[OH:1][C@H:2]1[C@@H:10]([OH:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1([NH:13][C:14](=[O:22])[O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[CH3:12].[H-].[Na+].[Cl-].[NH4+].C(OCC)(=O)C>C1COCC1>[OH:1][C@@H:2]1[C@H:10]([OH:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C@:3]1([NH:13][C:14](=[O:22])[O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[CH3:12].[OH:11][CH:10]1[CH:2]2[C:3]([CH3:12])([NH:13][C:14](=[O:15])[O:22]2)[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:9]1=2
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 90072640HCID 90072640、化合物

生成物 2

HCID 900724932-(trimethylsilyl)ethyl rac-[(1R,2S,3R)-2,3-dihydroxy-1-methyl-2,3-dihydro-1H-inden-1-yl]carbamateHCID 90073026
rac-(3aR,8S,8aR)-8-hydroxy-3a-methyl-3,3a,8,8a-tetrahydro-2H-indeno[1,2-d][1,3]oxazol-2-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 130 mg of 2-(trimethylsilyl)ethyl rac-[(2R,3S)-2,3-dihydroxy-1-methyl-2,3-dihydro-1H-inden-1-yl]carbamate in 4 ml of THF was added 70 mg of 55% sodium hydride under ice-cooling, followed by stirring at the same temperature for 1 hour. To the reaction mixture were added a saturated aqueous ammonium chloride solution and ethyl acetate to carry out a layer separation operation, followed by drying over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 70 mg of 2-(trimethylsilyl)ethyl rac-[(1R,2S,3R)-2,3-dihydroxy-1-methyl-2,3-dihydro-1H-inden-1-yl]carbamate and 45 mg of rac-(3aR,8S,8aR)-8-hydroxy-3a-methyl-3,3a,8,8a-tetrahydro-2H-indeno[1,2-d][1,3]oxazol-2-one.

後処理

  1. temperaturecooling
  2. customa layer separation operation
  3. dry with materialby drying over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-3121d4e780d9404b9e78699b502a3777
出典データセット
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09447090B2

反応ノート

読み込み中…

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