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Diethyl Ether → Tert-butyl 3-cyclohexyl-3-[(methylthio)methyl]-8-azabicyclo[3.2.1]octane-8-carboxylate

HRID 1178897
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HRID 1178897 반응식
[CH:1]1([C:7]2([CH2:22]OS(C)(=O)=O)[CH2:13][CH:12]3[N:14]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:9]([CH2:10][CH2:11]3)[CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:28][S-:29].[Na+].C(OCC)C>CN(C=O)C>[CH:1]1([C:7]2([CH2:22][S:29][CH3:28])[CH2:13][CH:12]3[N:14]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[CH:9]([CH2:10][CH2:11]3)[CH2:8]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1
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참가 물질

5

반응물 3

HCID 3283Diethyl EtherHCID 4378561Sodium methanethiolateHCID 86607399Tert-butyl 3-cyclohexyl-3-{[(methylsulfonyl)oxy]methyl}-8-azabicyclo[3.2.1]octane-8-carboxylate

생성물 1

HCID 58695800Tert-butyl 3-cyclohexyl-3-[(methylthio)methyl]-8-azabicyclo[3.2.1]octane-8-carboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

To a solution of tert-butyl 3-cyclohexyl-3-{[(methylsulfonyl)oxy]methyl}-8-azabicyclo[3.2.1]octane-8-carboxylate (3-4) (1.01 g, 2.69 mmol) in 50 mL of DMF was added sodium thiomethoxide (0.943 g, 13.5 mmol). The mixture was stirred at 60° C. for 3 days. After cooling to room temperature, 200 mL of diethyl ether was added. The solid was filtered and the filtrates were washed with water three times. The organics were dried over anhydrous MgSO4, filtered, and concentrated to give (3-5) as a clear yellow oil.

후처리

  1. temperatureAfter cooling to room temperature
  2. filtrationThe solid was filtered
  3. washthe filtrates were washed with water three times
  4. dry with materialThe organics were dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-00e912ccc32541879778f428edb28df7
출처 데이터셋
uspto-grants-2007_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07276520B2

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