Water → (2R,4R)-1-allyloxycarbonyl-2-[2-(imidazol-1-yl)ethyl]-4-(methanesulfonyloxy)pyrrolidine

HRID 975648Notes

Reaction equation

HRID 975648 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([OH:12])[CH2:9][C@H:8]1[CH2:13][CH2:14][N:15]1[CH:19]=[CH:18][N:17]=[CH:16]1)=[O:6])[CH:2]=[CH2:3].C(N(CC)CC)C.[CH3:27][S:28](Cl)(=[O:30])=[O:29].O>ClCCl>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][S:28]([CH3:27])(=[O:30])=[O:29])[CH2:9][C@H:8]1[CH2:13][CH2:14][N:15]1[CH:19]=[CH:18][N:17]=[CH:16]1)=[O:6])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 54134400(2R,4R)-1-allyloxycarbonyl-2-[2-(imidazol-1-yl)ethyl]-4-hydroxypyrrolidine

Product 1

HCID 54297291(2R,4R)-1-allyloxycarbonyl-2-[2-(imidazol-1-yl)ethyl]-4-(methanesulfonyloxy)pyrrolidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2R,4R)-1-allyloxycarbonyl-2-[2-(imidazol-1-yl)ethyl]-4-hydroxypyrrolidine (9.19 g) in dichloromethane (92 ml) were dropwise added triethylamine (5.79 ml) and methanesulfonyl chloride (3.22 ml) under ice cooling with stirring, and the solution was stirred at the same temperature for 1 hour. The reaction mixture was poured into water and extracted with dichloromethane. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was purified by silica gel chromatography eluting with a mixture of chloroform and methanol (9:1, V/V) to give (2R,4R)-1-allyloxycarbonyl-2-[2-(imidazol-1-yl)ethyl]-4-(methanesulfonyloxy)pyrrolidine (4.24 g).

Workup

  1. stirringthe solution was stirred at the same temperature for 1 hour
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with a mixture of chloroform and methanol (9:1, V/V)

Sources & evidence

ORD record
ord-77fa8bc185714a55af9a320600606718
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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