Dimethyl Sulfoxide → tert-Butyl 4-(2-oxoethyl)piperidine-1-carboxylate

HRID 1876840Notes

Reaction equation

HRID 1876840 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[OH:11][CH2:12][CH2:13][CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1.C(N(CC)CC)C>C(Cl)Cl>[O:11]=[CH:12][CH2:13][CH:14]1[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:18][CH2:19]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 8541401-(tert-Butoxycarbonyl)-4-(2-hydroxyethyl)piperidine

Product 1

HCID 10353694tert-Butyl 4-(2-oxoethyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dimethyl sulfoxide (7.43 mL, 0.105 mol) was added to oxalyl chloride (5.53 mL, 0.0654 mol) in methylene chloride (244.2 mL) at −78° C. After 10 min, tert-butyl 4-(2-hydroxyethyl)piperidine-1-carboxylate (10.0 g, 0.0436 mol) in methylene chloride (488.4 mL) was added and the resultant mixture was stirred at −78° C. for 30 min. Triethylamine (30.4 mL, 0.218 mol) was then added and the mixture was stirred for 5 h with the temperature allowed to gradually warm up to room temperature. After being quenched with water, the mixture was extracted with methylene chloride. The organic layers were combined, washed with brine, dried over MgSO4, evaporated to dryness and used directly in next step. LCMS (M+Na) 250.0.

Workup

  1. customAfter being quenched with water
  2. extractionthe mixture was extracted with methylene chloride
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-f50019bf76ba441d82dc4e0e1f19a3fe
Source dataset
uspto-grants-2012_11
Patent number
US08309718B2

Reaction notes

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