Triphenylstannane → HCID 13194414, 화합물

HRID 1719343노트

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HRID 1719343 반응식
[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]

참가 물질

5

반응물 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

생성물 1

HCID 13194414HCID 13194414, 화합물수율 62.3%

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-8810b2a410fc446ead6f30464f50d7b9
출처 데이터셋
uspto-grants-1985_09
특허 번호
US04539152

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