Triethylamine → Tert-butyl 4-methylsulfonyloxy-2-(methylsulfonyloxymethyl)pyrrolidine-1-carboxylate

HRID 1354847Notes

Reaction equation

HRID 1354847 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([OH:13])[CH2:10][CH:9]1[CH2:14][OH:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([O:13][S:24]([CH3:23])(=[O:26])=[O:25])[CH2:10][CH:9]1[CH2:14][O:15][S:24]([CH3:23])(=[O:26])=[O:25])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 4204845Tert-butyl 4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate

Product 1

HCID 73103977Tert-butyl 4-methylsulfonyloxy-2-(methylsulfonyloxymethyl)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of the diol (344) (12.7 g, 58.5 mmol) and triethylamine (5 equiv., 41 mL) in CH2Cl2 (200 mL) at 0° C. was added methanesulfonyl chloride (NsCl) (2.4 equiv., 10.9 mL). The resulting suspension was removed from the ice bath and allowed to warm to room temperature with stirring at which point TLC analysis indicated complete consumption of the starting material and conversion to a single spot of higher Rf (5% MeOH/CHCl3, stained with K2MnO4). The reaction was quenched by the addition of water (20 mL) with vigorous stirring. NaHCO3 (sat., aqueous, 200 mL) was added and the organic layer was separated, washed with brine, dried (MgSO4) and purified by flash chromatography (1–10% MeOH/CHCl3) to yield the desired compound (345) as a colorless oil.

Workup

  1. customThe resulting suspension was removed from the ice bath
  2. customconsumption of the starting material and conversion to a single spot of higher Rf (5% MeOH/CHCl3, stained with K2MnO4)
  3. customThe reaction was quenched by the addition of water (20 mL) with vigorous stirring
  4. additionNaHCO3 (sat., aqueous, 200 mL) was added
  5. customthe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. custompurified by flash chromatography (1–10% MeOH/CHCl3)

Sources & evidence

ORD record
ord-65e2c0ba7f094ab1bf747aeea457c21b
Source dataset
uspto-grants-2007_05
Patent number
US07223759B2

Reaction notes

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