Tributylstannane → methyl 2-[(3S,4R)-3-(1-hydroxy-1-methylethyl)-2-oxo-4-allylazetidin-1-yl]-3-methylbut-2-enoate

HRID 1719305ノート

反応式

HRID 1719305 の反応式
C([SnH](CCCC)CCCC)CCC.[OH:14][C:15]([C@:18]1([N+]#[C-])[C@@H:21]([CH2:22][CH:23]=[CH2:24])[N:20]([C:25](=[C:30]([CH3:32])[CH3:31])[C:26]([O:28][CH3:29])=[O:27])[C:19]1=[O:33])([CH3:17])[CH3:16].N(C(C)(C)C#N)=NC(C)(C)C#N>C1C=CC=CC=1>[OH:14][C:15]([C@@H:18]1[C@@H:21]([CH2:22][CH:23]=[CH2:24])[N:20]([C:25](=[C:30]([CH3:32])[CH3:31])[C:26]([O:28][CH3:29])=[O:27])[C:19]1=[O:33])([CH3:17])[CH3:16]

参加物

5

反応物 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 53962359methyl 2-[(3R,4R)-3-(1-hydroxy-1-methylethyl)-3-isocyano-2-oxo-4-allylazetidin-1-yl]-3-methylbut-2-enoate

生成物 1

HCID 22823199methyl 2-[(3S,4R)-3-(1-hydroxy-1-methylethyl)-2-oxo-4-allylazetidin-1-yl]-3-methylbut-2-enoate収率 96.6%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

Tributyltin hydride (0.707 ml) was added to a mixture of methyl 2-[(3R,4R)-3-(1-hydroxy-1-methylethyl)-3-isocyano-2-oxo-4-allylazetidin-1-yl]-3-methylbut-2-enoate (630 mg) and azobisisobutyronitrile (34 mg) in benzene (6 ml) at room temperature, and the mixture was refluxed for 15 minutes. The reaction mixture was cooled and chromatographed on silica gel (20 g) eluting with a mixture of hexane and ethyl acetate (3:1-1:1) to give a 3:1 mixture (559 mg) of methyl 2-[(3S,4R)-3-(1-hydroxy-1-methylethyl)-2-oxo-4-allylazetidin-1-yl]-3-methylbut-2-enoate and its (3R,4R)-isomer.

後処理

  1. temperaturethe mixture was refluxed for 15 minutes
  2. temperatureThe reaction mixture was cooled
  3. customchromatographed on silica gel (20 g)
  4. washeluting with a mixture of hexane and ethyl acetate (3:1-1:1)

出典と根拠

ORDレコード
ord-2572f6797bce49bf80c6ea2d6f575237
出典データセット
uspto-grants-1985_09
特許番号
US04539152

反応ノート

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