Pyridine → Carbonic acid 1-chloroethyl ester (R)-1-methylbutyl ester

HRID 2089649

반응식

HRID 2089649 반응식
Cl[C:2]([O:4][CH:5]([Cl:7])[CH3:6])=[O:3].N1C=CC=CC=1.[CH3:14][C@@H:15]([OH:19])[CH2:16][CH2:17][CH3:18].CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O>C1COCC1.CCCCCCC.C(OCC)(=O)C>[CH3:14][C@@H:15]([O:19][C:2](=[O:3])[O:4][CH:5]([Cl:7])[CH3:6])[CH2:16][CH2:17][CH3:18]

참가 물질

8

반응물 4

HCID 1049PyridineHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 5213051-Chloroethyl chloroformateHCID 7014876(2R)-pentan-2-ol

생성물 1

HCID 86677396Carbonic acid 1-chloroethyl ester (R)-1-methylbutyl ester

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매HCID 8900Heptane용매

실험 절차

To a mixture of 1-chloroethyl chloroformate (1.19 mL), pyridine (1.49 mL), and THF (100 mL), (R)-(−)-2-pentanol [CSA No. 31087-44-2] (1 mL) dissolved in THF (3 mL) was added at −78° C. After stirring the mixture overnight at room temperature, ethyl acetate and heptane were added to the reaction mixture. The resulting mixture was sequentially washed with 0.5 N hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution, water, and saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The resulting mixture was filtered, and the filtrate obtained was concentrated under reduced pressure to obtain the captioned compound (1.8 g) as a crude product.

후처리

  1. additionwas added at −78° C
  2. washThe resulting mixture was sequentially washed with 0.5 N hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution, water, and saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe resulting mixture was filtered
  5. customthe filtrate obtained
  6. concentrationwas concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-278f7c81a9bb4965b93b82b0fa33b030
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08436009B2

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