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

HRID 1583006Notes

Reaction equation

HRID 1583006 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-8a3c806700e94b0eb1ce49fdd6e595e6
Source dataset
uspto-grants-2004_05
Patent number
US06740663B2

Reaction notes

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