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

HRID 1664791ノート

反応式

HRID 1664791 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 30318Osmium Tetroxide触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-745ec34c9e824b948431e9b6bd430826
出典データセット
uspto-grants-2011_10
特許番号
US08039460B2

反応ノート

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