Dimethyl Sulfate → HCID 11847313, compound

HRID 1361285Notes

Reaction equation

HRID 1361285 reaction equation
[C:1]([N:8]1[CH2:12][CH2:11][C@@H:10]([OH:13])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH:14]([Li])([CH2:16]C)[CH3:15].COS(OC)(=O)=O>C(OCC)C.O>[C:1]([N:8]1[CH2:9][C@H:10]([OH:13])[CH2:11][C@@H:12]1[CH2:16][CH:14]=[CH2:15])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

6

Reactant 3

HCID 6497Dimethyl SulfateHCID 6544479tert-Butyl (3R)-3-hydroxypyrrolidine-1-carboxylateHCID 178418400CID 53628100

Product 1

HCID 11847313HCID 11847313, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-78 °C

Procedure

(3R)-1-BOC-3-hydroxypyrrolidine (1 g, 5.34 mmol) was dissolved in diethylether (50 ml), and filled with nitrogen. The reaction mixture was cooled to −78° C., N,N,N,N′-tetramethylethylenediamine (620 mg, 5.34 mmol) was added, and sec-butyllithium (1.4M cyclohexane solution 4.45 ml, 6.23 mmol) was slowly added. After being stirred for 30 min at the same temperature, dimethylsulfate (1.44 g, 10.68 mmol) was dissolved in diethylether (10 ml). The reaction solution was slowly heated to rt, diluted with water (12 ml), and extracted with diethylether. The organic extracts were dried over MgSO4, and the residue was purified by column chromatography (eluent, EtOAc/Hex=1/4) to give the title compound (840 mg, 70%).

Workup

  1. additionfilled with nitrogen
  2. temperatureThe reaction solution was slowly heated to rt
  3. extractionextracted with diethylether
  4. dry with materialThe organic extracts were dried over MgSO4
  5. customthe residue was purified by column chromatography (eluent, EtOAc/Hex=1/4)

Sources & evidence

ORD record
ord-905b627d762749ae9997d4a211029080
Source dataset
uspto-grants-2011_02
Patent number
US07879852B2

Reaction notes

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