Dimethyl Sulfoxide → HCID 23053108, compound

HRID 2167502Notes

Reaction equation

HRID 2167502 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 66%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent4×

Procedure

To a −50 to −60° C. cooled solution of oxalyl chloride (5.3 mL of a 2 M solution in methylene chloride, 10.6 mmol) in methylene chloride (5.3 mL) was added methyl sulfoxide (1.5 mL, 21.2 mmol) in methylene chloride (5 mL). After 3 min, a solution of 1-(3-methoxybenzyl)pyrrolidin-3-ol (2.0 g, 9.6 mmol) from Step A above in methylene chloride (10 mL) was added dropwise. After 25 min added triethylamine (6.8 mL, 4.8 mmol) and the reaction mixture was warmed to ambient temperature. Water (30 mL) was added and the aqueous layer was separated and extracted with methylene chloride (20 mL). The combined organic layers were dried over 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 (1.3 g, 66%) as a colorless oil: 1H NMR (DMSO-d6, 300 MHz) δ 7.24 (dd, J=8.1, 8.1 Hz, 1H), 6.91-6.81 (m, 3H), 3.74 (s, 3H), 3.65 (s, 2H), 2.87-2.82 (m, 4H), 2.37-2.32 (m, 2H).

Workup

  1. customthe aqueous layer was separated
  2. extractionextracted with methylene chloride (20 mL)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (methylene chloride to 1:1 methylene chloride/ethyl acetate)

Sources & evidence

ORD record
ord-ff80c7a22f9c43928d37420a75db5445
Source dataset
uspto-grants-2015_06
Patent number
US09045468B2

Reaction notes

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