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

HRID 1071507Notes

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

Conditions

Temperature: 0 °C

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 0° C. and methanesulfonyl chloride (180.19 mg, 1.57 mmol, 0.12 mL) was added via syringe. The reaction was stirred at 0° C. 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

temperatureto warm to room temp
stirringstir for 12 h
extractionthe aqueous layer was extracted three times with ethyl acetate
washThe combined organic layers were washed with water and brine
dry with materialthen dried over MgSO4
filtrationThe solution was filtered
customthe solvent removed under reduced pressure
customThe product was isolated by flash chromatography

Sources & evidence

ORD record: ord-47bf203ac9a4401183911c82d853fed4
Source dataset: uspto-grants-2005_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06906067B2

Reaction notes

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