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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
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HRID 64454 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 90072640HCID 90072640, 화합물

생성물 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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3121d4e780d9404b9e78699b502a3777
출처 데이터셋
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09447090B2

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