Methylenecyclobutane → HCID 57515834, 화합물

HRID 473346

반응식

HRID 473346 반응식
[Si:1]([O:8][C@@H:9]([C@@H:12]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:13][CH:14]=[CH2:15])[CH2:10][OH:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:24]=[C:25]1CC[CH2:26]1>Cl[Ru](=C1N(C2C(C)=CC(C)=CC=2C)CCN1C1C(C)=CC(C)=CC=1C)(Cl)(=CC1C=CC=CC=1)[P](C1CCCCC1)(C1CCCCC1)C1CCCCC1.ClCCCl.CCOC(C)=O>[Si:1]([O:8][C@@H:9]([C@@H:12]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:13][CH:14]=[C:15]1[CH2:26][CH2:25][CH2:24]1)[CH2:10][OH:11])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

참가 물질

6

반응물 2

HCID 14262MethylenecyclobutaneHCID 44240485HCID 44240485, 화합물

생성물 1

HCID 57515834HCID 57515834, 화합물수율 81%

시약·촉매·용매 3

HCID 178425456HCID 178425456, 화합물촉매HCID 111,2-Dichloroethane용매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

A solution of tert-butyl (2S,3S)-2-(tert-butyldimethylsilyloxy)-1-hydroxyhex-5-en-3-ylcarbamate (1.0 g, 2.9 mmol) and Grubbs Catalyst 2nd generation (0.12 g, 0.14 mmol) in DCE (6 mL) was treated with methylenecyclobutane (0.79 g, 12 mmol) and heated to 80° C. in a sealed vial overnight. The reaction mixture was diluted with EtOAc, washed with saturated NaHCO3 solution, and brine. The organics were dried over MgSO4 and concentrated under reduced pressure. Purification of the crude residue by column chromatography gave tert-butyl (2S,3S)-2-(tert-butyldimethylsilyloxy)-5-cyclobutylidene-1-hydroxypentan-3-ylcarbamate (0.900 g, 81% yield) as a 2:1 mixture with starting alkene.

후처리

  1. washwashed with saturated NaHCO3 solution, and brine
  2. dry with materialThe organics were dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customPurification of the crude residue by column chromatography

출처 및 근거

ORD 기록
ord-589e8bbd79c24becaf055c15e40106ee
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633315B2

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