Methanesulfonyl chloride → HCID 86707462, compound

HRID 338939Notes

Reaction equation

HRID 338939 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[O:10][C@@H:11]2[C@@H:15]([OH:16])[CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12]2)=[CH:5][CH:4]=1.[CH3:38][S:39](Cl)(=[O:41])=[O:40]>CN(C1C=CN=CC=1)C.ClCCl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[O:10][C@@H:11]2[C@@H:15]([O:16][S:39]([CH3:38])(=[O:41])=[O:40])[CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12]2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 86707461(3S,4S)-tert-butyl 3-(bis(4-methoxyphenyl)(phenyl)methoxy)-4-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 86707462HCID 86707462, compoundYield 99.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (3S,4S)-tert-butyl 3-(bis(4-methoxyphenyl)(phenyl)methoxy)-4-hydroxypyrrolidine-1-carboxylate (3.50 g, 6.92 mmol) and DMAP (4.23 g, 34.61 mmol) in dichloromethane (60 mL) at 0° C. in an ice bath was added methanesulfonyl chloride (2.69 mL, 34.61 mmol) dropwise. The resulting mixture was stirred at ambient temperature for 1 hour, cooled to 0° C. in an ice bath and quenched with water (15 mL). The layers were separated and the organic layer was washed with saturated sodium bicarbonate solution (60 mL), dried (MgSO4), filtered and concentrated under reduced pressure to give (3S,4S)-tert-butyl 3-(bis(4-methoxyphenyl)(phenyl)methoxy)-4-(methylsulfonyloxy)pyrrolidine-1-carboxylate (4.01 g, 99%).

Workup

  1. temperaturecooled to 0° C. in an ice bath
  2. customquenched with water (15 mL)
  3. customThe layers were separated
  4. washthe organic layer was washed with saturated sodium bicarbonate solution (60 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0a47ee0367e547e78f21a0e048a762c9
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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