Dimethyl Sulfoxide → Tert-butyl 3-oxopiperidine-1-carboxylate

HRID 2185961Notes

Reaction equation

HRID 2185961 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([OH:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CS(C)=O.O.C(N(CC)CC)C>C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C:10](=[O:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 8471TriethylamineHCID 5456991-Boc-3-hydroxypiperidine

Product 1

HCID 2756825Tert-butyl 3-oxopiperidine-1-carboxylateYield 57.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of give N-t-butoxycarbonyl-3-hydroxypiperidine (1.07 g, 5.23 mmol) in 1:1 dimethyl sulfoxide:water (50 ml) is added triethyl amine (3.7 ml) and sulfur trioxide pyridine complex (4.24 g, 26.6 mmol). The reaction mixture is stirred at 25° C. for 3 hrs. The reaction mixture is diluted with ethyl acetate, washed with 1 N KHSO4, water and brine, dried over sodium sulfate and concentrated in vacuo. The crude product is purified by flash chromatography (silica gel, 50% ethyl acetate in hexane) to give N-t-butoxycarbonyl-3-ketopiperidine (598 mg).

Workup

  1. washwashed with 1 N KHSO4, water and brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe crude product is purified by flash chromatography (silica gel, 50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-717307dd905148d5bf7382e99cfff5d5
Source dataset
uspto-grants-2002_06
Patent number
US06403612B2

Reaction notes

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