Acetic Acid → HCID 54036921、化合物

HRID 52275ノート

反応式

HRID 52275 の反応式
[NH2:1][C@@H:2]1[CH2:7][C:6]2[C:8]([O:13][CH3:14])=[CH:9][CH:10]=[C:11]([F:12])[C:5]=2[O:4][CH2:3]1.[CH3:15][C:16]([CH3:18])=O.C([BH3-])#N.[Na+].C(O)(=O)C>CO>[F:12][C:11]1[C:5]2[O:4][CH2:3][C@H:2]([NH:1][CH:16]([CH3:18])[CH3:15])[CH2:7][C:6]=2[C:8]([O:13][CH3:14])=[CH:9][CH:10]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 180AcetoneHCID 5003444Sodium cyanoborohydrideHCID 22871215(R)-8-fluoro-5-methoxy-3-aminochroman

生成物 1

HCID 54036921HCID 54036921、化合物

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

(R)-3-Amino-8-fluoro-5-methoxy-3,4-dihydro-2H-1-benzopyran (1.62 g, 8.21 mmol) was dissolved in anhydrous methanol (20 mL) and to this was acetone (6.0 mL, 82.1 mmol) added. The reaction was cooled (ice-bath) then sodium cyanoborohydride (0.92 g, 14.8 mmol) was added, the pH was adjusted to 4-5 with acetic acid and the reaction was allowed to stir at room temperature overnight. The solvent was removed in vacuo, the remains were taken into a 2M solution of NH3 and then extracted thrice with diethyl ether. The combined ether portions were dried (MgSO4), filtered, and the solvent removed in vacuo to give the crude residue that was used as is in the next reaction. GC-MS (70 eV) M=239 (81%).

後処理

  1. additionadded
  2. temperatureThe reaction was cooled (ice-bath)
  3. customThe solvent was removed in vacuo
  4. extractionextracted thrice with diethyl ether
  5. dry with materialThe combined ether portions were dried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent removed in vacuo

出典と根拠

ORDレコード
ord-39c00d1800c44318a85186ee35c4f668
出典データセット
uspto-grants-1997_04
特許番号
US05616610

反応ノート

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