Acetic Acid → (R)-3-(N-cyclopentylamino)-8-fluoro-5-methoxy-3,4-dihydro-2H-1-benzopyran

HRID 52285ノート

反応式

HRID 52285 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.[C:15]1(=O)[CH2:19][CH2:18][CH2:17][CH2:16]1.CC(O)=O.[BH3-]C#N.[Na+]>CO>[CH:15]1([NH:1][C@@H:2]2[CH2:7][C:6]3[C:8]([O:13][CH3:14])=[CH:9][CH:10]=[C:11]([F:12])[C:5]=3[O:4][CH2:3]2)[CH2:19][CH2:18][CH2:17][CH2:16]1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 8452CyclopentanoneHCID 5003444Sodium cyanoborohydrideHCID 22871215(R)-8-fluoro-5-methoxy-3-aminochroman

生成物 1

HCID 22871220(R)-3-(N-cyclopentylamino)-8-fluoro-5-methoxy-3,4-dihydro-2H-1-benzopyran収率 100%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of (R)-3-amino-8-fluoro-5-methoxy-3,4-dihydro-2H-1-benzopyran (0.7 g, 3.4 mmol), cyclopentanone (0.7 g, 8.3 mmol) and HOAc (0.2 g, 3.5 mmol) in methanol (25 mL), NaCNBH3 (0.7 g, 10 mmol) was added in portions at room temperature. The solution was stirred at room temperature over night. The methanol was evaporated. The residue was dissolved in EtOAc and washed with water. The organic layer was dried with Na2SO4 and the solvent was evaporated to give 0.9 g (100% yield) of the title compound as a colourless oil. GC indicated 99.6 purity. GC/MS (70 eV) M=265 (30%).

後処理

  1. customThe methanol was evaporated
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with water
  4. dry with materialThe organic layer was dried with Na2SO4
  5. customthe solvent was evaporated

出典と根拠

ORDレコード
ord-56cf6baf404b44228754487eeee27db1
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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