Methanesulfonyl chloride → Tert-butyl 3-(methanesulfonyloxy)pyrrolidine-1-carboxylate

HRID 2284047Notes

Reaction equation

HRID 2284047 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)C(C)C)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>C(Cl)Cl.CC(=O)OCC>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([O:13][S:24]([CH3:23])(=[O:26])=[O:25])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 44169391-Boc-3-pyrrolidinol

Product 1

HCID 4139999Tert-butyl 3-(methanesulfonyloxy)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 3-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (2000.00 mg; 10.68 mmol; 1.00 eq.) in DCM 10 ml added ethyl-diisopropyl-amine (2.49 ml; 13.89 mmol; 1.30 eq.), then added dropwise methanesulfonyl chloride (0.89 ml; 11.22 mmol; 1.05 eq.) at 0° C., the reaction mixture was stirred for overnight at RT. TLC (EA/HEX=7:3) showed staring material converted to desired completed. Diluted the reaction solution with EA, washed with brine, organic layer was dried, filtered through silica gel 10 g, most color material was absorbed on silica gel, the filtrate was evaporated off solvent, got residue as title compound directly using for the next step reaction, TLC was clean.

Workup

  1. washwashed with brine, organic layer
  2. customwas dried
  3. filtrationfiltered through silica gel 10 g, most color material
  4. customwas absorbed on silica gel
  5. customthe filtrate was evaporated off solvent
  6. customdirectly using for the next step reaction, TLC

Sources & evidence

ORD record
ord-d8a5be8550f54f5ba6eb6ddd8ff87906
Source dataset
uspto-grants-2015_09
Patent number
US09145392B2

Reaction notes

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