Dimethyl Sulfoxide → HCID 23053108, compound

HRID 2167505Notes

Reaction equation

HRID 2167505 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:23]=[CH:24][CH:25]=1)[CH2:16][N:17]1[CH2:21][CH2:20][CH:19]([OH:22])[CH2:18]1.C(N(CC)CC)C>C(Cl)Cl.O>[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:23]=[CH:24][CH:25]=1)[CH2:16][N:17]1[CH2:21][CH2:20][C:19](=[O:22])[CH2:18]1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 24904639HCID 24904639, compound

Product 1

HCID 23053108HCID 23053108, compoundYield 68.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of oxalyl chloride (14.6 mL, 170 mmol) in methylene chloride (100 mL) at −78° C., was added dimethyl sulfoxide (14.3 mL, 170 mmol). After 15 min, a solution of 1-(3-methoxybenzyl)pyrrolidin-3-ol (11.8 g, 56.8 mmol) from Step A above in methylene chloride (100 mL) was added dropwise. After 4 h, triethylamine (52 mL, 369 mmol) was added and the reaction mixture was warmed to ambient temperature. Water (50 mL) was added and the aqueous layer was separated and extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (methylene chloride to 1:1 methylene chloride/ethyl acetate) to provide 1-(3-methoxybenzyl)pyrrolidin-3-one (8.0 g, 68%) as a colorless oil: 1H NMR (CD3OD, 400 MHz) δ 7.26 (t, J=7.9 Hz, 1H), 7.00-6.92 (m, 2H), 6.89-6.81 (m, 1H), 3.81 (s, 3H), 3.72 (s, 2H), 2.99-2.95 (m, 2H), 2.94 (s, 2H), 2.41 (t, J=7.0 Hz, 2H); ESI MS (m/z) 206 [M+H]+.

Workup

  1. waitAfter 4 h
  2. customthe aqueous layer was separated
  3. extractionextracted with methylene chloride
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (methylene chloride to 1:1 methylene chloride/ethyl acetate)

Sources & evidence

ORD record
ord-2dd726f108ac44218f800185a6299a0d
Source dataset
uspto-grants-2015_06
Patent number
US09045468B2

Reaction notes

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