Sulfuric Acid → 3-Methyl-5-(1-methyl-2(S)-pyrrolidinyl)isoxazole

HRID 21767

반응식

HRID 21767 반응식
[BH4-].[Na+].[C:3]([N:13]1[CH2:20][CH2:19][CH2:18][C@H:14]1[C:15]([OH:17])=O)(OCC1C=CC=CC=1)=O.OS(O)(=O)=O>C1COCC1.CCOCC>[CH3:18][C:14]1[CH:15]=[C:15]([C@@H:14]2[CH2:18][CH2:19][CH2:20][N:13]2[CH3:3])[O:17][N:13]=1

참가 물질

6

반응물 3

HCID 1118Sulfuric AcidHCID 101987Benzyloxycarbonyl-L-prolineHCID 4311764Sodium borohydride

생성물 1

HCID 1193803-Methyl-5-(1-methyl-2(S)-pyrrolidinyl)isoxazole수율 88%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매2회HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

To a stirred suspension of sodium borohydride (7.59 g, 200 mmol) in 100 mL of THF cooled to 0° C. was added a solution of 20 g (80.28 mmol) of N-Cbz-L-proline, from step 24a above, in 50 mL of ether. To this solution was added dropwise a solution of 5 mL of H2SO4 in 20 mL of ether, with stirring and while maintaining the temperature below 20° C. The reaction mixture was warmed to room temperature and stirred for 16 hr. The reaction was quenched by the addition of 100 mL of methanol dropwise. The solvents were removed, 30 mL of 4N NaOH was added, and the mixture was extracted with ethyl acetate. The organic extract was dried over Na2SO4 and concentrated to afford the title product, 16.61 g (88 % yield).

후처리

  1. temperaturewhile maintaining the temperature below 20° C
  2. temperatureThe reaction mixture was warmed to room temperature
  3. stirringstirred for 16 hr
  4. customThe reaction was quenched by the addition of 100 mL of methanol dropwise
  5. customThe solvents were removed
  6. addition30 mL of 4N NaOH was added
  7. extractionthe mixture was extracted with ethyl acetate
  8. extractionThe organic extract
  9. dry with materialwas dried over Na2SO4
  10. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c9a6f38691244cecb730d2b45b58285c
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05424444

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