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

HRID 1434788Notes

Reaction equation

HRID 1434788 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-a82a4e790c0c4a94bd000c00a0679ec4
Source dataset
uspto-grants-2009_11
Patent number
US07615572B2

Reaction notes

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