Hydrochloric Acid → 1-Tert-butyl 2-methyl 4-(methanesulfonyloxy)pyrrolidine-1,2-dicarboxylate

HRID 1454267Notes

Reaction equation

HRID 1454267 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([OH:10])[CH2:7][N:6]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:4].C(N(CC)CC)C.[CH3:25][S:26](Cl)(=[O:28])=[O:27].Cl>C(Cl)Cl.CCCCCC.C(OCC)(=O)C>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([O:10][S:26]([CH3:25])(=[O:28])=[O:27])[CH2:7][N:6]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 51482991-Tert-butyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate

Product 1

HCID 147726801-Tert-butyl 2-methyl 4-(methanesulfonyloxy)pyrrolidine-1,2-dicarboxylate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

4-Hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-t-butyl ester 2-methyl ester (350.98 mg, 1.43 mmol) was dissolved in anhydrous DCM and triethylamine (434.11 mg, 4.29 mmol, 0.6 mL) was added under argon. The reaction mixture was cooled to 0EC and methanesulfonyl chloride (180.19 mg, 1.57 mmol, 0.12 mL) was added via syringe. The reaction was stirred at 0EC for 30 min and then allowed to warm to room temp and stir for 12 h. The reaction was slowly poured into a 1N HCl solution and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with water and brine then dried over MgSO4. The solution was filtered and the solvent removed under reduced pressure. The product was isolated by flash chromatography. (2:1 hexane-ethyl acetate) Yield 406.92 mg. C12H21NO7S MS m/e=323.1 (M+H).

Workup

  1. additionwas added via syringe
  2. stirringstir for 12 h
  3. extractionthe aqueous layer was extracted three times with ethyl acetate
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialthen dried over MgSO4
  6. filtrationThe solution was filtered
  7. customthe solvent removed under reduced pressure
  8. customThe product was isolated by flash chromatography

Sources & evidence

ORD record
ord-391fe4fd16914d1280ae3b10ff0e47c9
Source dataset
uspto-grants-2009_01
Patent number
US07479495B2

Reaction notes

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