Phosphorus oxychloride → Ethyl 3-methyl-1-(4-methylphenyl)sulfonyl-2,5-dihydropyrrole-2-carboxylate

HRID 1366937Notes

Reaction equation

HRID 1366937 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[C:10](O)([CH3:11])[CH2:9][CH2:8][N:7]1[S:13]([C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1)(=[O:15])=[O:14])=[O:5])[CH3:2].O=P(Cl)(Cl)Cl>N1C=CC=CC=1>[CH2:1]([O:3][C:4]([CH:6]1[C:10]([CH3:11])=[CH:9][CH2:8][N:7]1[S:13]([C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1)(=[O:14])=[O:15])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 15747129Ethyl 3-hydroxy-3-methyl-1-tosylpyrrolidine-2-carboxylate

Product 1

HCID 15747141Ethyl 3-methyl-1-(4-methylphenyl)sulfonyl-2,5-dihydropyrrole-2-carboxylateYield 88.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The pyrrolidine oil 82 (10.5 g, 32.11 mmol) was dissolved in pyridine (86 mL). POCl3 (7.48 mL, 80.27 mmol) was added dropwise and the resulting mixture stirred overnight at room temperature. The mixture was poured over ice, extracted with ether and washed with 5% aq. HCl, 5% sodium bicarbonate solution and water. The ether layer was dried over sodium sulfate, filtered and evaporated under reduced pressure to give the crude solid 83 (8.80 g, 88%). 1H-NMR (400 MHz, CDCl3): δ 1.28 (t, 3H), 1.69 (m, 3H), 2.43 (s, 3H), 4.10 (m, 1H), 4.20 (q, 2H), 4.21 (m, 1H), 7.31 (d, 2H), 7.75 (d, 2H) ppm. 13C-NMR (100 MHz, CDCl3): δ 13.58, 14.10, 21.56, 54.64, 61.62, 70.55, 110.02, 122.51, 127.51, 129.73, 169.87 ppm. DEPT (100 MHz, CDCl3): CH3 carbons: 13.58, 14.10, 21.56; CH2 carbons: 54.64, 61.62; CH carbons: 70.55, 122.51, 127.51, 129.73 ppm. LC/MS: 100%, m/z=309.

Workup

  1. additionThe mixture was poured over ice
  2. extractionextracted with ether
  3. washwashed with 5% aq. HCl, 5% sodium bicarbonate solution and water
  4. dry with materialThe ether layer was dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-a03d98ff22f54d6196bce2bb9ad577b6
Source dataset
uspto-grants-2011_02
Patent number
US07893098B2

Reaction notes

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