Sodium Hydroxide → HCID 69420232, compound

HRID 1178876Notes

Reaction equation

HRID 1178876 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:15][C:16]1[CH:17]=[C:18]([S:22]([N:25]([CH:27]2[CH2:31][CH2:30][C:29](=O)[CH2:28]2)[CH3:26])(=[O:24])=[O:23])[CH:19]=[CH:20][CH:21]=1.[F:33][C:34]([F:42])([F:41])[CH:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1.[OH-].[Na+]>ClCCCl>[CH3:15][C:16]1[CH:17]=[C:18]([S:22]([N:25]([CH3:26])[C@H:27]2[CH2:31][CH2:30][C@@H:29]([N:38]3[CH2:39][CH2:40][CH:35]([C:34]([F:42])([F:41])[F:33])[CH2:36][CH2:37]3)[CH2:28]2)(=[O:24])=[O:23])[CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 1364694-(Trifluoromethyl)piperidineHCID 5049666Sodium triacetoxyborohydrideHCID 69422275HCID 69422275, compound

Product 1

HCID 69420232HCID 69420232, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Sodium triacetoxyborohydride (340.4 mg, 1.61 mmol) was added to a solution of 3-((3,N-dimethyl)benzenesulfonamido)cyclopentan-1-one (280.7 mg, 1.05 mmol), and 4-trifluoromethylpiperidine (194.8 mg, 1.27 mmol) in 1,2-dichloroethane (10 ml). The resulting mixture was stirred at room temperature overnight (20 hours). 1M Aqueous sodium hydroxide (25 ml) was added and the mixture extracted with dichloromethane (2×10 ml). The combined extracts were dried (K2CO3) and evaporated. The residue was purified by medium pressure silica chromatography, eluting with 2.5% methanol in dichloromethane, to afford cis-3,N-dimethyl-N-(3-(4-trifluoromethylpiperidin-1-yl)cyclopentyl) -benzenesulfonamide (93.1 mg, 22%). A portion of this material was dissolved in ethyl acetate, warmed and treated with hydrogen chloride in diethyl ether to afford the title compound as a white crystalline solid; δH (400 MHz, CD3OD) 1.68 (2H, m), 1.83 (4H, m), 2.06-2.18 (4H, m), 2.44 (3H, s), 2.60 (1H, m), 2.79 (3H, s), 2.99 (2H, m), 3.51 (1H, m), 3.63 (1H, m), 3.69 (1H, m), 4.43 (1H, m), 7.47 (2H, m), 7.63 (2H, m); m/z (ES+) 405 ([M+H]+, 100%).

Workup

  1. extractionthe mixture extracted with dichloromethane (2×10 ml)
  2. dry with materialThe combined extracts were dried (K2CO3)
  3. customevaporated
  4. customThe residue was purified by medium pressure silica chromatography
  5. washeluting with 2.5% methanol in dichloromethane

Sources & evidence

ORD record
ord-ee1aab64eb1c43468e0a0a6b55807ca3
Source dataset
uspto-grants-2007_10
Patent number
US07276607B2

Reaction notes

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