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Ethanol → trans-4-Hydroxy-5-phenyl-2,3,4,5-tetrahydo spiro(benzothiepine-3,1'-cyclohexane)-1,1-dioxide

HRID 1583006
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HRID 1583006 반응식
[C:1]1([C:7]23[C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=4[S:17](=[O:25])(=[O:24])[CH2:16][C:10]4([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]4)[CH:8]2[O:9]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)C.[H][H]>[Pd].C(Cl)Cl>[OH:9][C@@H:8]1[C:10]2([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]2)[CH2:16][S:17](=[O:25])(=[O:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[C@H:7]1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
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참가 물질

6

반응물 3

HCID 702EthanolHCID 223252128b-Phenyl-1a,2,3,8b-tetrahydrospiro(benzothiepino[4,5-b]oxirene-2,1'-cyclohexane)-4,4-dioxideHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 59890377trans-4-Hydroxy-5-phenyl-2,3,4,5-tetrahydo spiro(benzothiepine-3,1'-cyclohexane)-1,1-dioxide수율 40.1%

시약·촉매·용매 2

HCID 23938Palladium촉매
HCID 6344Dichloromethane용매

실험 절차

A mixture of 0.5 g (1.4 mmoles) of 58, 20 ml of ethanol, 10 ml of methylene chloride and 0.4 g of 10% Pd/C catalyst was hydrogenated with 70 psi hydrogen for 3 h at room temperature. The crude reaction slurry was filtered through Celite and evaporated to dryness. The residue was purified by HPLC (10% EtOAc-Hexane, 25% EtOAc-Hexane). The first fraction was 300 mg (60%) as a white solid, mp 99-100° C. Proton NMR showed this was a trans isomer. The second fraction gave 200 mg of solid which was impure cis isomer.

후처리

  1. customThe crude reaction slurry
  2. filtrationwas filtered through Celite
  3. customevaporated to dryness
  4. customThe residue was purified by HPLC (10% EtOAc-Hexane, 25% EtOAc-Hexane)

출처 및 근거

ORD 기록
ord-8a3c806700e94b0eb1ce49fdd6e595e6
출처 데이터셋
uspto-grants-2004_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06740663B2

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