Methanesulfonyl chloride → N-[(Pyrrolidin-3-yl)methyl]methanesulfonamide

HRID 451241Notes

Reaction equation

HRID 451241 reaction equation
[NH2:1][CH2:2][C@H:3]1[CH2:7][CH2:6][N:5](C(OC(C)(C)C)=O)[CH2:4]1.[CH3:15][S:16](Cl)(=[O:18])=[O:17]>C(Cl)Cl.O>[NH:5]1[CH2:6][CH2:7][CH:3]([CH2:2][NH:1][S:16]([CH3:15])(=[O:18])=[O:17])[CH2:4]1

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 1515152tert-Butyl (3R)-3-(aminomethyl)pyrrolidine-1-carboxylate

Product 1

HCID 67001019N-[(Pyrrolidin-3-yl)methyl]methanesulfonamideYield 106.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

TEA (1.05 mL, 7.5 mmol) was added to a solution of (R)-3-(aminomethyl)-1-N-Boc-pyrrolidine (1 g, 5 mmol) in DCM (25 mL) at 0° C. Methanesulfonyl chloride (0.43 mL, 5.5 mmol) was then added. After stirring at 0° C. for 2 h, the reaction mixture was diluted with water. The organic phase was separated, dried (MgSO4), filtered and concentrated. The crude material was treated with 1M HCl in MeOH (25 mL) at RT and stirred at RT for 20 h. The volatiles were removed under reduced pressure to afford 0.95 g of 72 as a white solid.

Workup

  1. customThe organic phase was separated
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. additionThe crude material was treated with 1M HCl in MeOH (25 mL) at RT
  6. stirringstirred at RT for 20 h
  7. customThe volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-f1c934b756514405acb5a3a6b3eae39f
Source dataset
uspto-grants-2013_07
Patent number
US08487103B2

Reaction notes

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