Water → (R)-tert-butyl 3-(N-methylcyclopropanesulfonamido)pyrrolidine-1-carboxylate

HRID 527909Notes

Reaction equation

HRID 527909 reaction equation
[CH3:1][NH:2][C@@H:3]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4]1.[CH:15]1([S:18](Cl)(=[O:20])=[O:19])[CH2:17][CH2:16]1.CCN(C(C)C)C(C)C.O>C1COCC1>[CH3:1][N:2]([C@@H:3]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4]1)[S:18]([CH:15]1[CH2:17][CH2:16]1)(=[O:20])=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 2760919Cyclopropanesulfonyl chlorideHCID 45089543tert-Butyl (3R)-3-(methylamino)pyrrolidine-1-carboxylate

Product 1

HCID 86692139(R)-tert-butyl 3-(N-methylcyclopropanesulfonamido)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-tert-butyl 3-(methylamino)pyrrolidine-1-carboxylate (100 mg, 0.5 mmol) in 2.5 mL THF was added cyclopropanesulfonyl chloride (77 mg, 0.55 mmol) and DIPEA (0.10 mL, 0.60 mmol) at ambient temperature. The mixture was stirred at ambient temperature overnight. Water was added, and then extracted with EtOAc. The organic layers were combined washed with brine, dried over Na2SO4, and evaporated in vacuo to afford the crude title product which was used for the next step without further purification. MS (m/z): 305 (M+H)+.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layers were combined washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-0986bf05a58746b7902fd350e99fefc6
Source dataset
uspto-grants-2016_05
Patent number
US09346810B2

Reaction notes

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