Water → (2R,4R)-1-allyloxycarbonyl-2-(2-azidoethyl)-4-methanesulfonyloxypyrrolidine

HRID 975697Notes

Reaction equation

HRID 975697 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]=[N+:16]=[N-:17])=[O:6])[CH:2]=[CH2:3].C(N(CC)CC)C.[CH3:25][S:26](Cl)(=[O:28])=[O:27].O>ClCCl>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][S:26]([CH3:25])(=[O:28])=[O:27])[CH2:9][C@H:8]1[CH2:13][CH2:14][N:15]=[N+:16]=[N-:17])=[O:6])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 53738762(2R,4R)-1-allyloxycarbonyl-2-(2-azidoethyl)-4-hydroxypyrrolidine

Product 1

HCID 54350989(2R,4R)-1-allyloxycarbonyl-2-(2-azidoethyl)-4-methanesulfonyloxypyrrolidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2R,4R)-1-allyloxycarbonyl-2-(2-azidoethyl)-4-hydroxypyrrolidine (20.0 g) and triethylamine (15.2 ml) in dichloromethane (300 ml) was added methanesulfonyl chloride (7.8 ml) under ice-cooling. After stirring for 1 hour, water was poured into the mixture. The organic layer was separated and the aqueous layer was extracted twice with dichloromethane. The combined organic layer was washed with 1N hydrochloric acid, sat. sodium bicarbonate, water and brine, dried over magnesium sulfate and evaporated under reduced pressure to give (2R,4R)-1-allyloxycarbonyl-2-(2-azidoethyl)-4-methanesulfonyloxypyrrolidine (15.3 g).

Workup

  1. temperaturecooling
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted twice with dichloromethane
  4. washThe combined organic layer was washed with 1N hydrochloric acid, sat. sodium bicarbonate, water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-9772586844744df8bd15d74716e11117
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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