8-[Dihydro-furan-(2z)-ylidenemethanesulfonyl]-2-(4-trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decan-1-one → 8-(Tetrahydro-furan-2-ylmethanesulfonyl)-2-(4-trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decan-1-one

HRID 2194192Notes

Reaction equation

HRID 2194192 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3]/[C:2]/1=[CH:6]/[S:7]([N:10]1[CH2:31][CH2:30][C:13]2([C:17](=[O:18])[N:16]([C:19]3[CH:24]=[CH:23][C:22]([O:25][C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=3)[CH2:15][CH2:14]2)[CH2:12][CH2:11]1)(=[O:9])=[O:8]>CO>[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[CH2:6][S:7]([N:10]1[CH2:11][CH2:12][C:13]2([C:17](=[O:18])[N:16]([C:19]3[CH:24]=[CH:23][C:22]([O:25][C:26]([F:28])([F:29])[F:27])=[CH:21][CH:20]=3)[CH2:15][CH2:14]2)[CH2:30][CH2:31]1)(=[O:9])=[O:8]

Participants

3

Reactant 1

HCID 595779038-[Dihydro-furan-(2z)-ylidenemethanesulfonyl]-2-(4-trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decan-1-one

Product 1

HCID 595781018-(Tetrahydro-furan-2-ylmethanesulfonyl)-2-(4-trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decan-1-oneYield 36%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

8-[Dihydro-furan-(2Z)-ylidenemethanesulfonyl]-2-(4-trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decan-1-one (described in example 213, 15 mg, 0.03 mmol) was dissolved in MeOH (2 mL). The flask was evacuated and then purged with argon. Pd/C (2 mg) was added in one portion and the flask was evacuated, then purged with hydrogen three times. The reaction mixture was then stirred at room temperature for 16 h. The mixture was filtered through Celite® and the filtrate was then concentrated in vacuo and purified by flash column chromatography (3:2 AcOEt/heptane) to give 8-(tetrahydro-furan-2-ylmethanesulfonyl)-2-(4-trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decan-1-one (5 mg, 33%) as a white solid. MS (ESI): 463.3 (MH+).

Workup

  1. customThe flask was evacuated
  2. custompurged with argon
  3. additionPd/C (2 mg) was added in one portion
  4. customthe flask was evacuated
  5. custompurged with hydrogen three times
  6. filtrationThe mixture was filtered through Celite®
  7. concentrationthe filtrate was then concentrated in vacuo
  8. custompurified by flash column chromatography (3:2 AcOEt/heptane)

Sources & evidence

ORD record
ord-6c7bfe3147fa4564902da55070c8e19e
Source dataset
uspto-grants-2012_12
Patent number
US08329904B2

Reaction notes

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