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

HRID 1719277ノート

反応式

HRID 1719277 の反応式
[CH2:1]([C@H:4]1[N:7]([C:8](=[C:13]([CH3:15])[CH3:14])[C:9]([O:11][CH3:12])=[O:10])[C:6](=[O:16])[CH:5]1Cl)[CH:2]=[CH2:3].C([SnH](CCCC)CCCC)CCC.N(C(C)(C)C#N)=NC(C)(C)C#N.C(=O)(O)[O-].[Na+]>C1C=CC=CC=1.C(OCC)(=O)C>[CH2:1]([C@H:4]1[N:7]([C:8](=[C:13]([CH3:15])[CH3:14])[C:9]([O:11][CH3:12])=[O:10])[C:6](=[O:16])[CH2:5]1)[CH:2]=[CH2:3]

参加物

7

反応物 4

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 516892Sodium BicarbonateHCID 54283209methyl 2-[(4R)-4-allyl-3-chloro-2-oxoazetidin-1-yl]-3-methylbut-2-enoate

生成物 1

HCID 54326273methyl 2-[(4R)-2-oxo-4-allylazetidin-1-yl]-3-methylbut-2-enoate収率 87%

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of methyl 2-[(4R)-4-allyl-3-chloro-2-oxoazetidin-1-yl]-3-methylbut-2-enoate (600 mg), tributyltinhydride (0.97 ml) and 2,2'-azobis-(2-methylpropionitrile) (40 mg) in benzene (16 ml) was refluxed for 1.5 hours. The reaction mixture was poured into a mixture of ethyl acetate (30 ml) and dilute aqueous sodium bicarbonate. The organic layer was separated, and washed with brine, dried over magnesium sulfate and evaporated in vacuo. The oily residue was chromatographed on silica gel (10 g) eluting with a mixture of hexane and ethyl acetate (10:1-10:3) to give methyl 2-[(4R)-4-allyl-2-oxoazetidin-1-yl]-3-methylbut-2-enoate (452 mg) as an oil.

後処理

  1. temperaturewas refluxed for 1.5 hours
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe oily residue was chromatographed on silica gel (10 g)
  7. washeluting with a mixture of hexane and ethyl acetate (10:1-10:3)

出典と根拠

ORDレコード
ord-0dcd254e8e174307a7cd84a42a0ef5d3
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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