Triethylamine → [1-({[tert-Butyl(dimethyl)silyl]oxy}methyl)cyclopropyl]methyl methanesulfonate

HRID 906437

Reaction equation

HRID 906437 reaction equation
[Si:1]([O:8][CH2:9][C:10]1([CH2:13][OH:14])[CH2:12][CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>C(Cl)Cl.O>[CH3:22][S:23]([O:14][CH2:13][C:10]1([CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH2:11][CH2:12]1)(=[O:25])=[O:24]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59000904(1-(((tert-Butyldimethylsilyl)oxy)methyl)cyclopropyl)methanol

Product 1

HCID 59000927[1-({[tert-Butyl(dimethyl)silyl]oxy}methyl)cyclopropyl]methyl methanesulfonate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of [1-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopropyl]methanol (Example 34c, 5.37 g) dissolved in DCM (20 mL) was treated with triethylamine (6.92 mL) at 0° C. before adding methanesulfonyl chloride (2.321 mL) under nitrogen. The resulting mixture was stirred at 0° C. for 30 min. The reaction mixture was diluted with water (100 mL), and extracted with DCM (250 mL). The organics were dried (MgSO4), filtered and evaporated. The crude product was purified (SiO2 chromatography, elution 50% isohexane in diethyl ether). Pure fractions were evaporated to dryness to afford the subtitle compound (5.37 g) as an oil.

Workup

  1. extractionextracted with DCM (250 mL)
  2. dry with materialThe organics were dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude product was purified
  6. wash(SiO2 chromatography, elution 50% isohexane in diethyl ether)
  7. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-2be7449450db4b7bb51f95b6aae5ad43
Source dataset
uspto-grants-2011_09
Patent number
US08012980B2

Linked notes

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