Triphenylstannane → HCID 13194414、化合物

HRID 1719343ノート

反応式

HRID 1719343 の反応式
[CH3:1][C:2]1([CH3:17])[O:9][CH2:8][CH2:7][C@H:6]2[N:3]1[C:4](=[O:16])[C:5]2([C:12]([OH:15])([CH3:14])[CH3:13])[N+]#[C-].C1([SnH](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(C)(C)C#N)=NC(C)(C)C#N>C1C=CC=CC=1>[CH3:1][C:2]1([CH3:17])[O:9][CH2:8][CH2:7][C@H:6]2[N:3]1[C:4](=[O:16])[C@H:5]2[C:12]([OH:15])([CH3:13])[CH3:14]

参加物

5

反応物 3

HCID 6460TriphenylstannaneHCID 6547AzobisisobutyronitrileHCID 18599214(6R,7RS)-2,2-dimethyl-7-(1-hydroxy-1-methylethyl)-7-isocyano-1-aza-3-oxabicyclo[4.2.0]-octan-8-one

生成物 1

HCID 13194414HCID 13194414、化合物収率 62.3%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

A solution of (6R,7RS)-2,2-dimethyl-7-(1-hydroxy-1-methylethyl)-7-isocyano-1-aza-3-oxabicyclo[4.2.0]-octan-8-one (920 mg), triphenyltin hydride (1.694 g) and azobisisobutyronitrile (63.4 mg) in benzene (46 ml) was heated at 50° C. for thirty minutes under a nitrogen atmosphere. The mixture was cooled to ambient temperature. The precipitates were filtered off and washed with benzene. The filtrate and washings were combined and chromatographed on silica gel (27.6 g, eluting with 10 to 25% acetone in dichloromethane) to give a crude product mixture, which was re-chromatographed on silica gel (46 g; 230-400 mesh, eluting with a 6:1 to 1:2 mixture of hexane and ethyl acetate) to give 513 mg of (6R,7R)-2,2-dimethyl-7-(1-hydroxy-1-methylethyl)-1-aza-3-oxabicyclo[4.2.0]octan-8-one after crystallization from diisopropyl ether and 170 mg of its 7S isomer as a crystalline solid.

後処理

  1. filtrationThe precipitates were filtered off
  2. washwashed with benzene
  3. customchromatographed on silica gel (27.6 g, eluting with 10 to 25% acetone in dichloromethane)
  4. customto give a crude product mixture, which
  5. customwas re-chromatographed on silica gel (46 g
  6. wash230-400 mesh, eluting with a 6:1 to 1:2 mixture of hexane and ethyl acetate)

出典と根拠

ORDレコード
ord-8810b2a410fc446ead6f30464f50d7b9
出典データセット
uspto-grants-1985_09
特許番号
US04539152

反応ノート

読み込み中…