Ammonium Hydroxide → 1-Benzyloxycarbonyl-4-(2-methylsulfinylphenyl)piperidine

HRID 1108029Notes

Reaction equation

HRID 1108029 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[S:23][CH3:24])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:33])C=1.[NH4+].[OH-]>C(Cl)Cl>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[S:23]([CH3:24])=[O:33])[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 111106201-Benzyloxycarbonyl-4(2-methylthiophenyl)piperidine

Product 1

HCID 226222471-Benzyloxycarbonyl-4-(2-methylsulfinylphenyl)piperidineYield 18.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of Step 3 (2.55 g) in CH2Cl2 (30 mL) was cooled to 0° C. and treated with mCPBA (60%, 2.16 g) and stirred for 1 h. The reaction mixture was treated with ice (20 g), saturated NH4OH solution (20 mL) and stirred for 10 minutes. The organic layer was separated and the aqueous layer re-extracted with CH2Cl2 (2×30 mL). The combined organic portions were dried over MgSO4, filtered and evaporated to give a gum. Silica gel chromatography, eluting with EtOAc/CH2Cl2 mixtures, gave 1-benzyloxycarbonyl-4-(2-methylsulfinylphenyl)piperidine (0.5 g).

Workup

  1. stirringstirred for 10 minutes
  2. customThe organic layer was separated
  3. extractionthe aqueous layer re-extracted with CH2Cl2 (2×30 mL)
  4. dry with materialThe combined organic portions were dried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give a gum
  8. washSilica gel chromatography, eluting with EtOAc/CH2Cl2 mixtures

Sources & evidence

ORD record
ord-b5afc93ad9de4fcbbec93f7d34495a02
Source dataset
uspto-grants-2000_05
Patent number
US06063926

Reaction notes

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