Water → HCID 86603713, compound

HRID 226403Notes

Reaction equation

HRID 226403 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[CH2:5][N:6]1[CH2:10][CH2:9][C@@H:8]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:7]1.N1C=CC=CC=1.[CH3:28][S:29](Cl)(=[O:31])=[O:30].O>C(Cl)Cl>[CH3:28][S:29]([NH:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[CH2:5][N:6]1[CH2:10][CH2:9][C@@H:8]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:7]1)(=[O:31])=[O:30]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 86603711HCID 86603711, compound

Product 1

HCID 86603713HCID 86603713, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl [(3R)-1-(3-aminobenzyl)-3-pyrrolidinyl]carbamate (659 mg) in CH2Cl2 (6.6 mL) was added pyridine (274 uL) and methanesulfonyl chloride (193 uL), which was stirred at room temperature for 20 hours. To the resultant was added H2O. The mixture was extracted with 1-butanol. The organic phase was washed brine, dried Na2SO4, filtered, and evaporated in vacuo. The residue was purified by column chromatography on silica gel to give tert-butyl [(3R)-1-{3-[(methylsulfonyl)amino]benzyl}-3-pyrrolidinyl]carbamate (845 mg) as pale yellow amorphous.

Workup

  1. extractionThe mixture was extracted with 1-butanol
  2. washThe organic phase was washed brine, dried Na2SO4
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-e64c295463714ad0902a1ffd204d123f
Source dataset
uspto-grants-2009_07
Patent number
US07557127B2

Reaction notes

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