Triphenylphosphine → (1E,3aR,4E,7aS)-4-(bromomethylene)-1-ethylidene-octahydro-7a-methyl-1H-indene

HRID 1922635노트

반응식

HRID 1922635 반응식
[Br:1]/[CH:2]=[C:3]1\[CH2:4][CH2:5][CH2:6][C@@:7]2([CH3:15])[C@H:11]\1[CH2:10][CH2:9][C@@H:8]2[C@@H:12](O)[CH3:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC(N=NC(OCC)=O)=O)C>O1CCCC1>[Br:1]/[CH:2]=[C:3]1/[C@H:11]2[C@:7]([CH3:15])([CH2:6][CH2:5][CH2:4]/1)/[C:8](=[CH:12]/[CH3:13])/[CH2:9][CH2:10]2

참가 물질

5

반응물 3

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 59456539(S)-1-{(E,3S,3aS,7aR)-7-(bromomethylene)-octahydro-3a-methyl-1H-indene-3-yl}ethanol2회

생성물 1

HCID 59456521(1E,3aR,4E,7aS)-4-(bromomethylene)-1-ethylidene-octahydro-7a-methyl-1H-indene수율 44.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Under a nitrogen atmosphere, a solution of (S)-1-{(E,3S,3aS,7aR)-7-(bromomethylene)-octahydro-3a-methyl-1H-indene-3-yl}ethanol (Compound 18: 52.4 mg, 0.1918 mmol) and triphenylphosphine (126 mg, 0.4795 mmol) in tetrahydrofuran (0.3 ml) was cooled in an ice bath, and azodicarboxylic acid diethyl ester (2.2 M in toluene, 223.4 μl, 0.4915 mmol) was added dropwise thereto. The reaction mixture was stirred in the ice bath for 10 minutes and at room temperature for 21 hours, and then evaporated under reduced pressure. The obtained crude product was purified by flash column chromatography to obtain (1E,3aR,4E,7aS)-4-(bromomethylene)-1-ethylidene-octahydro-7a-methyl-1H-indene (21.8 mg, 44.6%).

후처리

  1. customevaporated under reduced pressure
  2. customThe obtained crude product
  3. customwas purified by flash column chromatography

출처 및 근거

ORD 기록
ord-45d9ab5d91d64b2ba5c527c086942bbe
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173824B2

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