Water → HCID 66698120, compound

HRID 1619878Notes

Reaction equation

HRID 1619878 reaction equation
[CH3:1][NH2:2].[CH2:3]([O:10][C:11]([N:13]1[CH2:17][CH2:16][CH:15]([S:18](Cl)(=[O:20])=[O:19])[CH2:14]1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O>C1COCC1>[CH3:1][NH:2][S:18]([CH:15]1[CH2:16][CH2:17][N:13]([C:11]([O:10][CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[O:12])[CH2:14]1)(=[O:20])=[O:19]

Participants

5

Reactant 3

HCID 962WaterHCID 6329MethylamineHCID 53229936Benzyl 3-(chlorosulfonyl)pyrrolidine-1-carboxylate

Product 1

HCID 66698120HCID 66698120, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Methylamine (40 wt % in H2O, 1 mL) was added to a solution of 3-chlorosulfonyl-pyrrolidine-1-carboxylic acid benzyl ester (256 mg, 0.843 mmol) in THF (1 mL) at 0° C. The mixture was stirred at 0° C. for 10 min, and then warmed to room temperature and stirred for 2 hrs. Water was added and the phases were separated. The aqueous phase was extracted with CH2Cl2 (2×), the combined organic extracts were dried (Na2SO4), and the solvent was removed under vacuum. Chromatography on neutral alumina, eluting with CH2Cl2/MeOH (99:1 to 95:5), gave benzyl 3-[(methylamino)sulfonyl]-1-pyrrolidinecarboxylate (173 mg, 69%): 1H NMR (CDCl3) δ 7.36-7.29 (m, 5H), 5.14 (d, J=1.9 Hz, 2H), 4.27 (d, J=42.6 Hz, 1H), 3.80-3.70 (m, 4H), 3.50 (m, 1H), 2.82 (d, J=4.9 Hz, 3H), 2.35 (m, 2H).

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred for 2 hrs
  3. customthe phases were separated
  4. extractionThe aqueous phase was extracted with CH2Cl2 (2×)
  5. dry with materialthe combined organic extracts were dried (Na2SO4)
  6. customthe solvent was removed under vacuum
  7. washChromatography on neutral alumina, eluting with CH2Cl2/MeOH (99:1 to 95:5)

Sources & evidence

ORD record
ord-f1e7f92c59d047a1b7ccb6d137126b69
Source dataset
uspto-grants-2014_07
Patent number
US08772287B2

Reaction notes

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