Pyridine → 4-Chloromethyl-4-methyl-oxazolidin-2-one

HRID 1023475Notes

Reaction equation

HRID 1023475 reaction equation
C([O:5][C:6]([NH:8][C:9]([CH3:14])([CH2:12][OH:13])[CH2:10]O)=O)(C)(C)C.N1C=CC=CC=1.S(Cl)([Cl:24])(=O)=O>C(Cl)Cl.C(OCC)C>[CH3:14][C:9]1([CH2:10][Cl:24])[CH2:12][O:13][C:6](=[O:5])[NH:8]1

Participants

6

Reactant 3

HCID 1049PyridineHCID 24648Sulfuryl chlorideHCID 11593669tert-butyl N-(1,3-dihydroxy-2-methylpropan-2-yl)carbamate

Product 1

HCID 553038834-Chloromethyl-4-methyl-oxazolidin-2-oneYield 28.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-(tert-butoxycarbonylamino)-2-methyl-1,3-propanediol (2.28 g, 11.1 mmol) in CH2Cl2 (100 ml) and pyridine (2.0 ml, 25 mmol) was cooled to 0° C. and sulfuryl chloride (1.0 ml, 12 mmol) in CH2Cl2 (20 ml) was added dropwise over 15 min. The solution was warmed to RT over 4 h, diluted with diethyl ether (300 ml), washed with 3× 100 ml 5% NaHSO4, 3× 100 ml sat. NaHCO3, 1× 100 ml sat. NaCl, dried on MgSO4, and evaporated. The crude material was purified by flash chromatography (30-100% EtOAc in hexanes) to afford the title compound as a clear oil (470 mg, 3.14 mmol, 28.3%). 1H NMR (CDCl3, 400 MHz) δ 1.49 (s, 3H), 3.55 (s, 2H), 4.12 (d, 1H, J=9.2 Hz), 4.33 (d, 1H, J=8.8 Hz), 5.9 (br s, 1H). APCI/ESI calculated for C5H8ClNO2: 149.02. Found: 150 (MH+).

Workup

  1. washwashed with 3× 100 ml 5% NaHSO4, 3× 100 ml sat. NaHCO3, 1× 100 ml sat. NaCl
  2. customdried on MgSO4
  3. customevaporated
  4. customThe crude material was purified by flash chromatography (30-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-6e072c46c4f84b6b914a234d9ab9243f
Source dataset
uspto-grants-2014_05
Patent number
US08722715B2

Reaction notes

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