Sodium Sulfite → Benzyl 4-[3-cyclopropyl-1-(ethoxycarbonyl)-3-oxopropyl]piperidine-1-carboxylate

HRID 1664791노트

반응식

HRID 1664791 반응식
[CH:1]1([C:4](=C)[CH2:5][CH:6]([CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:19])[CH2:14][CH2:13]2)[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1.I([O-])(=O)(=O)=[O:30].[Na+].S([O-])([O-])=O.[Na+].[Na+].C(=O)(O)[O-].[Na+]>O1CCCC1.O.[Os](=O)(=O)(=O)=O>[CH:1]1([C:4](=[O:30])[CH2:5][CH:6]([CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:19])[CH2:14][CH2:13]2)[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1

참가 물질

8

반응물 4

HCID 24437Sodium SulfiteHCID 516892Sodium BicarbonateHCID 23667635Sodium periodateHCID 67440127Benzyl 4-[3-cyclopropyl-1-(ethoxycarbonyl)but-3-en-1-yl]piperidine-1-carboxylate

생성물 1

HCID 67439783Benzyl 4-[3-cyclopropyl-1-(ethoxycarbonyl)-3-oxopropyl]piperidine-1-carboxylate

시약·촉매·용매 3

HCID 30318Osmium Tetroxide촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

Osmium tetroxide (2.5 wt. % in t-BuOH; 17 uL, 0.001 mmol) was added to a solution of benzyl 4-[3-cyclopropyl-1-(ethoxycarbonyl)but-3-en-1-yl]piperidine-1-carboxylate (173 mg, 0.45 mmol) in tetrahydrofuran (2 mL). Sodium periodate (290 mg, 1.35 mmol) in water (1.5 mL) was added to the reaction mixture. After 18 h, saturated aqueous sodium sulfite and saturated aqueous sodium bicarbonate were added and the mixture was extracted with ethyl acetate (4×). The combined organic extracts were dried over magnesium sulfate, filtered and concentrated to give the title compound. MS 388.1 (M+1).

후처리

  1. extractionthe mixture was extracted with ethyl acetate (4×)
  2. dry with materialThe combined organic extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-745ec34c9e824b948431e9b6bd430826
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08039460B2

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