Potassium Carbonate → 1-t-Butoxycarbonyl-4-phenyl-4-[3,5-bis(trifluoromethyl)benzylsulphinylmethyl]piperidine

HRID 2258530Notes

Reaction equation

HRID 2258530 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][C:22]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)([CH2:25][S:26][CH2:27][C:28]2[CH:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[C:30]([C:38]([F:41])([F:40])[F:39])[CH:29]=2)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].C(=O)([O-])[O-].[K+].[K+]>ClCCl>[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][C:22]([C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)([CH2:25][S:26]([CH2:27][C:28]2[CH:33]=[C:32]([C:34]([F:36])([F:37])[F:35])[CH:31]=[C:30]([C:38]([F:41])([F:39])[F:40])[CH:29]=2)=[O:6])[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 22922286HCID 22922286, compound

Product 1

HCID 229223051-t-Butoxycarbonyl-4-phenyl-4-[3,5-bis(trifluoromethyl)benzylsulphinylmethyl]piperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

m-Chloroperoxybenzoic acid (80-90%, 0.4 g) was added to a solution of Example 3 (1 g) in dichloromethane (20 ml) containing potassium carbonate (0.5 g), at 0° C. The solution was stirred for 30 min, diluted with dichloromethane (20 ml), washed with water, dried (Na2SO4) and removal of the solvent in vacuo gave an off white solid. The solid was recrystallised from diethyl ether/petrol giving 1-t-butoxycarbonyl-4-phenyl-4-[3,5-bis(trifluoromethyl)benzylsulphinylmethyl]piperidine as a white solid, m.p. 123°-134° C., m/z (CI+) 567 (M+ +NH4+). Found: C, 57.00; H, 5.18; N, 2.36. C26H29NO3SF6 requires C, 56.82; H, 5.32; N, 2.55.

Workup

  1. customat 0° C
  2. washwashed with water
  3. customdried
  4. custom(Na2SO4) and removal of the solvent in vacuo
  5. customgave an off white solid
  6. customThe solid was recrystallised from diethyl ether/petrol

Sources & evidence

ORD record
ord-374b074dece2475c9182e0e843edfdbc
Source dataset
uspto-grants-1997_08
Patent number
US05661162

Reaction notes

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