m-Chloroperbenzoic acid → Tert-butyl 4-{3-[4-(methylsulfonyl)benzyl]-1,2,4-oxadiazol-5-yl}piperidine-1-carboxylate

HRID 1593000Notes

Reaction equation

HRID 1593000 reaction equation
CS[C:3]1[CH:27]=[CH:26][C:6]([CH2:7][C:8]2[N:12]=[C:11]([CH:13]3[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]3)[O:10][N:9]=2)=[CH:5][CH:4]=1.Cl[C:29]1C=CC=C(C(OO)=O)C=1.[S:39](S([O-])=O)([O-:42])(=O)=[O:40].[Na+].[Na+]>ClCCl>[CH3:29][S:39]([C:3]1[CH:27]=[CH:26][C:6]([CH2:7][C:8]2[N:12]=[C:11]([CH:13]3[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20])[CH2:15][CH2:14]3)[O:10][N:9]=2)=[CH:5][CH:4]=1)(=[O:42])=[O:40]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 656671Sodium PyrosulfiteHCID 68710908Tert-butyl 4-{3-[4-(methylthio)benzyl]-1,2,4-oxadiazol-5-yl}piperidine-1-carboxylate

Product 1

HCID 68709899Tert-butyl 4-{3-[4-(methylsulfonyl)benzyl]-1,2,4-oxadiazol-5-yl}piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-{3-[4(methylthio)benzyl]-1,2,4-oxadiazol-5-yl}piperidine-1-carboxylate (3.10 g, 7.96 mmol) (Method E, step 1) was dissolved in dichloromethane(100 mL), at room temperature, under argon. 3-Chloroperbenzoic acid (60% wt, 6.87 g, 23.88 mmol) was added portionwise and stirred for 1 hour. Sodium metabisulfite (1M, 250 mL) was added and stirred and the organics separated and washed with 1N sodium hydroxide and brine, dried (MgSO4) and solvents evaporated to a clear oil which crystallised upon addition of diethyl ether (50 mL). The solid was filtered, washed with a minimum of diethyl ether and dried to give tert-butyl 4-{3-[4-(methylsulfonyl)benzyl]-1,2,4-oxadiazol-5-yl}piperidine-1-carboxylate as a white fluffy solid (2.61 g, 78% yield); NMR (CDCl3): 1.46 (9H, s), 1.61 (3H, s), 1.79 (2H, m), 2.04 (2H, m), 2.93 (2H, m), 3.04 (3H, s), 4.15 (2H, s), 7.53 (2H, d), 7.90 (2H, d).

Workup

  1. stirringstirred
  2. customthe organics separated
  3. washwashed with 1N sodium hydroxide and brine
  4. dry with materialdried (MgSO4) and solvents
  5. customevaporated to a clear oil which
  6. customcrystallised upon addition of diethyl ether (50 mL)
  7. filtrationThe solid was filtered
  8. washwashed with a minimum of diethyl ether
  9. customdried

Sources & evidence

ORD record
ord-2ee3802730f84843a85754a4f707604c
Source dataset
uspto-grants-2007_11
Patent number
US07294636B2

Reaction notes

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