Triethylamine → HCID 118383472, compound

HRID 2202702Notes

Reaction equation

HRID 2202702 reaction equation
O[C:2]([CH:5]1[C:14](=[O:15])[N:8]2[C:9]([CH3:13])([CH3:12])[O:10][CH2:11][C@H:7]2[CH2:6]1)([CH3:4])[CH3:3].CS(Cl)(=O)=O.C(N(CC)CC)C>C(Cl)Cl>[CH3:12][C:9]1([CH3:13])[N:8]2[C:14](=[O:15])[C:5](=[C:2]([CH3:4])[CH3:3])[CH2:6][C@@H:7]2[CH2:11][O:10]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chloride2×HCID 118383701HCID 118383701, compound

Product 1

HCID 118383472HCID 118383472, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of (7aR)-6-(2-hydroxypropan-2-yl)-3,3-dimethyltetrahydropyrrolo[1,2-c]oxazol-5(3H)-one (5.06 g, 23.73 mmol) in DCM (50 mL) at room temperature was added methanesulfonyl chloride (2.75 mL, 35.6 mmol) followed by triethylamine (16.50 mL, 119 mmol) and then heated at 55° C. for 1 h. The resulting mixture was treated with additional methanesulfonyl chloride (2.75 mL, 35.6 mmol) and heated for another 1 h. The reaction mixture was allowed to cool to room temperature, quenched with water (50 mL) and extracted with DCM (2×100 mL). The combined extracts were washed with brine, dried over MgSO4, filtered and concentrated to provide crude (R)-3,3-dimethyl-6-(propan-2-ylidene)tetrahydropyrrolo[1,2-c]oxazol-5(3H)-one as a brown oil, which was used in the next step without purification. m/z (ESI, +ve) 196 (M+H).

Workup

  1. temperatureheated for another 1 h
  2. temperatureto cool to room temperature
  3. customquenched with water (50 mL)
  4. extractionextracted with DCM (2×100 mL)
  5. washThe combined extracts were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-0e55d94695c446a5b43a23a67e21bad2
Source dataset
uspto-grants-2016_06
Patent number
US09365522B2

Reaction notes

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