Methanesulfonyl chloride → methyl (2S,4S)-1-BOC-4-[(4,4-dimethylcyclohexyl)(methylsulfonyl)amino]pyrrolidine-2-carboxylate

HRID 1361309Notes

Reaction equation

HRID 1361309 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@H:8]([NH:10][CH:11]2[CH2:16][CH2:15][C:14]([CH3:18])([CH3:17])[CH2:13][CH2:12]2)[CH2:7][N:6]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[O:4].[CH3:26][S:27](Cl)(=[O:29])=[O:28]>C(Cl)Cl>[C:19]([N:6]1[CH2:7][C@@H:8]([N:10]([CH:11]2[CH2:16][CH2:15][C:14]([CH3:18])([CH3:17])[CH2:13][CH2:12]2)[S:27]([CH3:26])(=[O:29])=[O:28])[CH2:9][C@H:5]1[C:3]([O:2][CH3:1])=[O:4])([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 66970872Methyl(2S,4S)-1-BOC-4-[(4,4-dimethylcyclohexyl)amino]pyrrolidine-2-carboxylate

Product 1

HCID 66971207methyl (2S,4S)-1-BOC-4-[(4,4-dimethylcyclohexyl)(methylsulfonyl)amino]pyrrolidine-2-carboxylateYield 528.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl (2S,4S)-1-BOC-4-[(4,4-dimethylcyclohexyl)amino]pyrrolidine-2-carboxylate (2.37 g, 6.7 mmol) prepared in Step A of Example A1 in DCM (10 ml) was added TEA (1.36 g, 13.4 mmol), slowly added dropwise methanesulfonylchloride (104 mg, 0.91 mmol) at 0° C., and stirred at rt for 30 min. After the reaction finished, the solvent was concentrated in vacuo, the residue was extracted with water and EtOAc. The organic layer was dried over MgSO4, concentrated in vacuo, and purified by column chromatography (eluent: EtOAc/Hex ═1/1) to give the title compound (2.08 g, 72%).

Workup

  1. concentrationthe solvent was concentrated in vacuo
  2. extractionthe residue was extracted with water and EtOAc
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. custompurified by column chromatography (eluent: EtOAc/Hex ═1/1)

Sources & evidence

ORD record
ord-f60457c97b7a460993f110d5bc9654fe
Source dataset
uspto-grants-2011_02
Patent number
US07879852B2

Reaction notes

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