Ammonium formate → (R)-8-fluoro-5-methoxy-3-aminochroman

HRID 1738312노트

반응식

HRID 1738312 반응식
C([N:8]([C@@H:16]1[CH2:21][C:20]2[C:22]([O:27][CH3:28])=[CH:23][CH:24]=[C:25]([F:26])[C:19]=2[O:18][CH2:17]1)CC1C=CC=CC=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.C1COCC1.[Pd]>[NH2:8][C@@H:16]1[CH2:21][C:20]2[C:22]([O:27][CH3:28])=[CH:23][CH:24]=[C:25]([F:26])[C:19]=2[O:18][CH2:17]1

참가 물질

6

반응물 2

HCID 2723923Ammonium formateHCID 20640362(R)-3-(N,N-Dibenzylamino)-8-fluoro-5-methoxy-3,4-dihydro-2H-1-benzopyran

생성물 1

HCID 22871215(R)-8-fluoro-5-methoxy-3-aminochroman수율 91.4%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
50 °C

실험 절차

(R)-3-(N,N-Dibenzylamino)-8-fluoro-5-methoxy-3,4-dihydro-2H-1-benzopyran (13.0 g, 34.4 mmol) was dissolved in 265 mL methanol and 115 mL THF. To this was 10% Pd/C (4 g) and ammonium formate (51.5 g, 0.817 mol) added. The reaction was heated to 50° C. for 2.5 h. The reaction was filtered and the solvent was removed in vacuo, the remains were taken into a 2M solution of NaOH and then extracted twice with ether. The combined ether portions were treated with brine, dried (Na2SO4), filtered, and the solvent removed in vacuo to give 6.2 g (91% yield) of the title compound as a clear oil. [α]21D =-15.3° (C=1, CHCl3). GC-MS (70 eV) M=197 (51%).

후처리

  1. filtrationThe reaction was filtered
  2. customthe solvent was removed in vacuo
  3. extractionextracted twice with ether
  4. additionThe combined ether portions were treated with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent removed in vacuo

출처 및 근거

ORD 기록
ord-2f94e825691844c18c4aaf7fc8a258ce
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05962514

반응 노트

불러오는 중…