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

HRID 1738312ノート

反応式

HRID 1738312 の反応式
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

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

(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%).

後処理

  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

出典と根拠

ORDレコード
ord-2f94e825691844c18c4aaf7fc8a258ce
出典データセット
uspto-grants-1999_10
特許番号
US05962514

反応ノート

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