m-Chloroperbenzoic acid → tert-Butyl 4-(propane-2-sulfinyl)piperidine-1-carboxylate

HRID 341548Notes

Reaction equation

HRID 341548 reaction equation
[CH3:1][CH:2]([S:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)[CH3:3].ClC1C=CC=C(C(OO)=[O:26])C=1>C(Cl)Cl>[CH3:3][CH:2]([S:4]([CH:5]1[CH2:6][CH2:7][N:8]([C:11]([O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:12])[CH2:9][CH2:10]1)=[O:26])[CH3:1]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 86710528HCID 86710528, compound2×

Product 1

HCID 86710529tert-Butyl 4-(propane-2-sulfinyl)piperidine-1-carboxylateYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

tert-Butyl 4-(propan-2-ylsulfanyl)piperidine-1-carboxylate (prepared in an analogous manner to Intermediate 245, 0.160 g, 0.62 mmol) was dissolved in DCM (3 mL) and cooled to 0 C. m-Chloroperbenzoic acid (0.138 g, 0.62 mmol) was added, the mixture was warmed to room temperature and stirred for 17 h. Further m-chloroperbenzoic acid (0.040 g, 0.18 mmol) was added and the mixture was stirred at room temperature for 3 h. The mixture was then diluted with DCM (10 mL) and washed with saturated aq. sodium thiosulfate (10 mL). The organic layer was separated and purified by FCC, eluting with 50-100% EtOAc in heptane followed by 10% MeOH in EtOAc to afford the title compound as a colourless oil (0.124 g, 73%). Method C HPLC-MS: MH+ requires m/z=276 Found: m/z=298 (M+Na), Rt=1.14 min (100%).

Workup

  1. temperaturecooled to 0 C
  2. stirringthe mixture was stirred at room temperature for 3 h
  3. washwashed with saturated aq. sodium thiosulfate (10 mL)
  4. customThe organic layer was separated
  5. custompurified by FCC
  6. washeluting with 50-100% EtOAc in heptane

Sources & evidence

ORD record
ord-64b8f2dcbdb240e6bcdad0640126cccf
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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