4-Toluenesulfonyl chloride → 1-(Tert-butyl) 2-methyl (2S,4S)-4-(tosyloxy)pyrrolidine-1,2-dicarboxylate

HRID 2185408Notes

Reaction equation

HRID 2185408 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH3:12][O:13][C:14](=[O:28])[C@@H:15]1[CH2:19][C@H:18]([OH:20])[CH2:17][N:16]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]>CN(C)C1C=CN=CC=1.ClCCl>[CH3:12][O:13][C:14](=[O:28])[C@@H:15]1[CH2:19][C@H:18]([O:20][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[CH2:17][N:16]1[C:21]([O:23][C:24]([CH3:25])([CH3:27])[CH3:26])=[O:22]

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 10752873N-Boc-cis-4-hydroxy-L-proline methyl ester

Product 1

HCID 134257681-(Tert-butyl) 2-methyl (2S,4S)-4-(tosyloxy)pyrrolidine-1,2-dicarboxylateYield 69%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

4-Dimethylaminopyridine (2.28 g) and p-toluenesulfonyl chloride (2.66 g) were added to a cold (0° C.) stirred solution of N-tert-butoxycarbonyl-cis-4-hydroxy-L-proline methyl ester (J, 2.76 g) in dichloromethane (50 mL). After stirring at room temperature for 16 hr, the solvent was removed in vacuo. The residue was diluted with ethyl acetate, and washed with 0.5 M saturated citric acid, water, and brine. The organic layer was dried over anhydrous sodium sulfate and evaporated in vacuo to give the title compound (3.10 g) as a pale yellow oil: 1H NMR (400 MHz, CDCl3) δ 1.35-1.52 (m, 9H), 2.30-2.53 (m, 2H), 2.46 (s, 3H), 3.51-3.78 (m, 2H), 3.68-3.69 (s, 3H), 4.30-4.56 (m, 1H), 5.00-5.09 (m, 1H), 7.32-7.38 (m, 1H), and 7.74-7.79 (m, 1H).

Workup

  1. customthe solvent was removed in vacuo
  2. additionThe residue was diluted with ethyl acetate
  3. washwashed with 0.5 M saturated citric acid, water, and brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-a0c30e18d9a242f8878e01f14300d5aa
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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