Benzyl chloroformate → Benzyl (3-fluoropiperidin-4-yl)carbamate

HRID 2214967노트

반응식

HRID 2214967 반응식
C([NH:8][C@H:9]1[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][C@H:10]1[F:22])C1C=CC=CC=1.Cl[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25]>C(O)C.[OH-].[OH-].[Pd+2]>[CH2:27]([O:26][C:24]([NH:8][CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH:10]1[F:22])=[O:25])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

참가 물질

5

반응물 2

HCID 10387Benzyl chloroformateHCID 11312869cis-4-Benzylamino-1-tert-butoxycarbonyl-3-fluoropiperidine

생성물 1

HCID 21948945Benzyl (3-fluoropiperidin-4-yl)carbamate수율 98%

시약·촉매·용매 2

HCID 9942167Palladium hydroxide촉매HCID 702Ethanol용매

실험 절차

cis-(+)-4-Benzylamino-1-tert-butoxycarbonyl-3-fluoropiperidine [(3e); Enantiomer 1] (15.0 g, 0.049 mole) in ethanol (300 ml) was hydrogenated over 20% palladium hydroxide on carbon (4g) at 30 psi for 5 h, then filtered through Celite® and evaporated. The crude amine was dissolved in ethyl acetate (100 mL), saturated sodium hydrogen carbonate solution (100 mL) was added followed by benzyl chloroformate (7.6 mL, 0.53 mole)and the mixture stirred vigorously for 4 h. The organic phase was separated dried and evaporated. The product was dissolved in DCM (75 mL) and stirred with TFA (20 mL) for 4 h then evaporated. The residue was basified with sodium carbonate solution, extracted with 10% methanol in DCM and the extracts dried and evaporated to give a white solid (12.1 g, 98%), [α]D+61.1° (MeOH).

후처리

  1. filtrationfiltered through Celite®
  2. customevaporated
  3. dissolutionThe crude amine was dissolved in ethyl acetate (100 mL)
  4. additionsaturated sodium hydrogen carbonate solution (100 mL) was added
  5. customThe organic phase was separated
  6. customdried
  7. customevaporated
  8. dissolutionThe product was dissolved in DCM (75 mL)
  9. stirringstirred with TFA (20 mL) for 4 h
  10. customthen evaporated
  11. extractionextracted with 10% methanol in DCM
  12. customthe extracts dried
  13. customevaporated

출처 및 근거

ORD 기록
ord-f8133123fc084ab686a9b8c79284cc91
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07109213B2

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