Dichloromethane → tert-Butyl 3-(((methylsulfonyl)oxy)methyl)pyrrolidine-1-carboxylate

HRID 541909Notes

Reaction equation

HRID 541909 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4]1.C(Cl)Cl.[CH3:18][S:19](Cl)(=[O:21])=[O:20].C(N(CC)CC)C>O>[CH3:18][S:19]([O:1][CH2:2][CH:3]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4]1)(=[O:21])=[O:20]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 5237175tert-Butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate

Product 1

HCID 4183641tert-Butyl 3-(((methylsulfonyl)oxy)methyl)pyrrolidine-1-carboxylateYield 76.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into the reaction flask was added tert-butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate (0.80 g, 4.0 mmol), methylene chloride (20 mL), and methanesulfonyl chloride (0.55 g, 4.8 mmol). The mixture was stirred at 0° C. when triethylamine (1.4 mL) was slowly added. The reaction mixture was stirred at rt for 2 h, followed by the addition of water (5 mL). The aqueous layer was extracted twice with methylene chloride. The combined organic layers were dried over Na2SO4, filtered and concentrated to give the desired product (0.85 g crude) which was used without further purification.

Workup

  1. additionwas slowly added
  2. extractionThe aqueous layer was extracted twice with methylene chloride
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8389db3983d545ef8fc34a1650d12e97
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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