Hydrochloric Acid → HCID 59252699, compound

HRID 1641298Notes

Reaction equation

HRID 1641298 reaction equation
[C:1]([N:4]([C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=1)[C:5]1([C:18]([O:20]CC)=O)[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7][CH2:6]1)(=[O:3])[CH3:2].C([N-]C(C)C)(C)C.[Li+].O.Cl>C1COCC1.CCOC(C)=O>[CH2:11]([N:8]1[CH2:9][CH2:10][C:5]2([N:4]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=3)[C:1](=[O:3])[CH2:2][C:18]2=[O:20])[CH2:6][CH2:7]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 2724682Lithium diisopropylamideHCID 66737933HCID 66737933, compound

Product 1

HCID 59252699HCID 59252699, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a 0° C. solution of 0.86 g (2.2 mmol) ethyl 4-[acetyl(3-fluorophenyl)amino]-1-benzylpiperidine-4-carboxylate in 1 mL THF was added 3.2 mL (6.5 mmol, 2M solution in heptane, THF, ethylbenzene) lithium diisopropylamide solution and the reaction mixture was allowed to slowly warm to rt and stirred for an additional 14 hr. To this mixture was added 50 mL water and 50 mL EtOAc and the pH was adjusted to pH=6 with 1N HCl (approx 11 mL). The aqueous layer was extracted 3×100 mL EtOAc and the combined extracts washed with 100 mL brine, dried over MgSO4, filtered, and concentrated to give 8-benzyl-1-(3-fluorophenyl)-1,8-diazaspiro[4.5]decane-2,4-dione as a solid. 1H NMR (CDCl3, 400 MHz) δ 7.44 (ddd, J=8.06, 8.06 and 6.23 Hz, 1H); 7.14-7.30 (m, 6H); 6.95 (br d, J=7.88 Hz, 1H); 6.89 (ddd, J=9.16, 2.02, and 2.02 Hz, 1H); 3.52 (s, 2H); 3.26 (s, 2H); 2.73 (m, 2H); 2.65 (m, 2H); 1.85 (br m, 4H). Electrospray mass spectrum M+H=353.1

Workup

  1. extractionThe aqueous layer was extracted 3×100 mL EtOAc
  2. washthe combined extracts washed with 100 mL brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9e437397766a419cacb70c93079dd6a0
Source dataset
uspto-grants-2012_02
Patent number
US08114887B2

Reaction notes

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