Triethylamine → Tert-butyl 3-((methanesulfonyloxy)methyl)azetidine-1-carboxylate

HRID 528752Notes

Reaction equation

HRID 528752 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([CH2:12][OH:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([CH2:12][O:13][S:22]([CH3:21])(=[O:24])=[O:23])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10583745tert-Butyl 3-(hydroxymethyl)azetidine-1-carboxylate

Product 1

HCID 21959416Tert-butyl 3-((methanesulfonyloxy)methyl)azetidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 0.3 g (1.6 mmol) 3-hydroxymethyl-azetidine-1-carboxylic acid tert-butyl ester (route 15, step a) in 3 mL DCM at 0° C. were added 0.33 mL (2.4 mmol) triethylamine and 0.19 mL (2.4 mmol) methanesulfonyl chloride. The reaction was allowed to warm to room temperature and stirred for 3 hours. 10 mL DCM was added and the mixture was washed with H2O (3×15 mL). The organic phase was dried over Na2SO4. After filtration and evaporation of the solvent the product was purified by column chromatography (silica, heptane/EtOAc 7:3 to 6:4).

Workup

  1. washthe mixture was washed with H2O (3×15 mL)
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationAfter filtration and evaporation of the solvent the product
  4. customwas purified by column chromatography (silica, heptane/EtOAc 7:3 to 6:4)

Sources & evidence

ORD record
ord-d355a306e6e04627baec3947622e7ecc
Source dataset
uspto-grants-2016_05
Patent number
US09346816B2

Reaction notes

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