Triethylamine → HCID 22843271, compound

HRID 1029649Notes

Reaction equation

HRID 1029649 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([OH:13])[CH2:10][C@H:9]1[CH3:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:15][S:16](Cl)(=[O:18])=[O:17].C(N(CC)CC)C>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][S:16]([CH3:15])(=[O:18])=[O:17])[CH2:10][C@H:9]1[CH3:14])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 14117010114676-93-6

Product 1

HCID 22843271HCID 22843271, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2R,4R)-1-(tert-butoxycarbonyl)-4-hydroxy-2-methylpyrrolidine (1.92 g) and methanesulfonyl chloride (955 μl) in dichloromethane (30 ml) was added dropwise triethylamine (1.99 ml) at 0° C. After one hour, the reaction mixture was washed in turn with 1N-hydrochloric acid and brine and the organic layer was dried over magnesium sulfate. Evaporation of the solvent gave an oil, which was chromatographed on silica gel (200 ml) eluting with a mixture of hexane and ethyl acetate (1:1, V/V) to give (2R,4R)-1-(tert-butoxycarbonyl)-4-methanesulfonyloxy-2-methylpyrrolidine (2.49 g).

Workup

  1. washthe reaction mixture was washed in turn with 1N-hydrochloric acid and brine
  2. dry with materialthe organic layer was dried over magnesium sulfate
  3. customEvaporation of the solvent
  4. customgave an oil, which
  5. customwas chromatographed on silica gel (200 ml)
  6. washeluting with a mixture of hexane and ethyl acetate (1:1, V/V)

Sources & evidence

ORD record
ord-6c30f1ff030646268a616c82e032db54
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

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