Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → (S)-tert-butyl 1-(1-fluorocyclohexyl)-3-hydroxypropan-2-ylcarbamate

HRID 451758노트

반응식

HRID 451758 반응식
[F:1][C:2]1([CH2:8][C@H:9]2[CH2:13][O:12]C(C)(C)[N:10]2[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>CO>[F:1][C:2]1([CH2:8][C@H:9]([NH:10][C:16](=[O:17])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22])[CH2:13][OH:12])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

참가 물질

4

반응물 2

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 59201498(S)-tert-butyl 4-((1-fluorocyclohexyl)methyl)-2,2-dimethyloxazolidine-3-carboxylate

생성물 1

HCID 68713243(S)-tert-butyl 1-(1-fluorocyclohexyl)-3-hydroxypropan-2-ylcarbamate수율 28.5%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

(S)-tert-butyl 4-((1-fluorocyclohexyl)methyl)-2,2-dimethyloxazolidine-3-carboxylate (1.1 g, 3.50 mmol, 1.0 equiv) was dissolved in methanol (30 mL). To this mixture was added camphorsulfonic acid (202 mg, 0.875 mmol, 0.5 equiv) and the solution was stirred at rt for 3 h. After this time the starting material was consumed. Satd aq NaHCO3 was added and the methanol was removed in vacuo. The aqueous residue was extracted with EtOAc (3×10 mL) and the combined organic extracts were washed with brine, dried over Na2SO4, filtered and evaporated. Flash chromatography on silica, eluting with 0-47% EtOAc in hexanes, afforded (S)-tert-butyl 1-(1-fluorocyclohexyl)-3-hydroxypropan-2-ylcarbamate (275 mg).

후처리

  1. customAfter this time the starting material was consumed
  2. additionSatd aq NaHCO3 was added
  3. customthe methanol was removed in vacuo
  4. extractionThe aqueous residue was extracted with EtOAc (3×10 mL)
  5. washthe combined organic extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. washFlash chromatography on silica, eluting with 0-47% EtOAc in hexanes

출처 및 근거

ORD 기록
ord-ce8de18e6b4b4148b49ea5d57474ec36
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08487108B2

반응 노트

불러오는 중…