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

HRID 52260노트

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HRID 52260 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

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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 2 M 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-5873e019fbd4454a97065d1d92f5c096
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616610

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