Triethylamine → HCID 15117248, compound

HRID 1029638Notes

Reaction equation

HRID 1029638 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([OH:13])[CH2:10][C@H:9]1[CH2:14][O:15][CH3:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:17][S:18](Cl)(=[O:20])=[O:19].C(N(CC)CC)C>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][S:18]([CH3:17])(=[O:20])=[O:19])[CH2:10][C@H:9]1[CH2:14][O:15][CH3:16])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 15117247HCID 15117247, compound

Product 1

HCID 15117248HCID 15117248, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,4R)-1-(tert-butoxycarbonyl)-4-hydroxy-2-methoxymethylpyrrolidine (2.8 g) and methanesulfonyl chloride (1.12 ml) in dichloromethane (30 ml) was added dropwise triethylamine (2.38 ml) at 0° C. After 30 minutes, the reaction mixture was washed in turn with 1N-hydrochloric acid, water and brine. The organic layer was dried over magnesium sulfate and evaporated to give an oil, which was chromatographed on silica gel (300 ml) eluting with a mixture of hexane and ethyl acetate (1:1, V/V) to give (2S,4R)-1-(tert-butoxycarbonyl)-4-methanesulfonyloxy-2-methoxymethylpyrrolidine (3.61 g).

Workup

  1. washthe reaction mixture was washed in turn with 1N-hydrochloric acid, water and brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customevaporated
  4. customto give an oil, which
  5. customwas chromatographed on silica gel (300 ml)
  6. washeluting with a mixture of hexane and ethyl acetate (1:1, V/V)

Sources & evidence

ORD record
ord-c463677a81bd4cbe81c728ef97a77e8f
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

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