Dimethyl Sulfoxide → 1-Tert-butyl 3-methyl 5-oxopiperidine-1,3-dicarboxylate

HRID 931253Notes

Reaction equation

HRID 931253 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[OH:11][CH:12]1[CH2:17][N:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:15][CH:14]([C:25]([O:27][CH3:28])=[O:26])[CH2:13]1.C(N(CC)CC)C>ClCCl>[O:11]=[C:12]1[CH2:17][N:16]([C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])[CH2:15][CH:14]([C:25]([O:27][CH3:28])=[O:26])[CH2:13]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 457909591-tert-Butyl 3-methyl 5-hydroxypiperidine-1,3-dicarboxylate

Product 1

HCID 683092691-Tert-butyl 3-methyl 5-oxopiperidine-1,3-dicarboxylateYield 98.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of dimethylsulfoxide (2.2 mL, 41.46 mmol) in dry dichloromethane (50 mL) at −78° C. was added dropwise at oxalyl chloride (1.57 mL, 18.2 mmol). After 10 min, a solution of 1-tert-butyl 3-methyl 5-hydroxypiperidine-1,3-dicarboxylate (4.3 g, 16.59 mmol) in dichloromethane was added dropwise. After 15 min, triethylamine (6.92 mL, 49.7 mmol) was added dropwise and the reaction mixture was then allowed to warm to room temperature. After 3 h, the mixture was diluted with dichloromethane and washed with water, dried over sodium sulfate, filtered and concentrated under reduced pressure to afford 1-tert-butyl 3-methyl 5-oxopiperidine-1,3-dicarboxylate (4.2 g) which was used in the next step without further purification.

Workup

  1. waitAfter 15 min
  2. waitAfter 3 h
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f2f67a82a51a4c02adffd7aa4ae3e2ef
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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