Acetic Acid → HCID 22871221、化合物

HRID 52286ノート

反応式

HRID 52286 の反応式
[CH:1]1([NH:6][C@@H:7]2[CH2:12][C:11]3[C:13]([O:18][CH3:19])=[CH:14][CH:15]=[C:16]([F:17])[C:10]=3[O:9][CH2:8]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.CC(O)=O.[C:24]1(=O)[CH2:27][CH2:26][CH2:25]1.[BH3-]C#N.[Na+]>CO>[CH:1]1([N:6]([C@@H:7]2[CH2:12][C:11]3[C:13]([O:18][CH3:19])=[CH:14][CH:15]=[C:16]([F:17])[C:10]=3[O:9][CH2:8]2)[CH:24]2[CH2:27][CH2:26][CH2:25]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 14496CyclobutanoneHCID 5003444Sodium cyanoborohydrideHCID 22871220(R)-3-(N-cyclopentylamino)-8-fluoro-5-methoxy-3,4-dihydro-2H-1-benzopyran

生成物 1

HCID 22871221HCID 22871221、化合物収率 53%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of (R)-3-(N-cyclopentylamino)-8-fluoro-5- methoxy-3,4-dihydro-2H-1-benzopyran (0.9 g, 3.4 mmol), HOAc (0.22 g, 3.6 mmol) and cyclobutanone (2g, 30 mmol) in methanol (25 mL), were NaCNBH3 (1 g, 16 mmol) added in portions at room temperature. After stirring for four days GC indicated 37% product. pH was adjusted to 5 (HOAc)and additional (1 g, 15 mmol) cyclobutanone was added. After stirring for further 6 days, GC indicated 64% conversion. The solvent was evaporated and the residue worked up by extraction. Flash chromatography (EtOAc/P-ether, 1+1), gave 0.53 g (53% yield) of the title compound as a colourless oil. GC/MS (70 eV) M=319 (3%).

後処理

  1. additionadded in portions at room temperature
  2. additionwas added
  3. customThe solvent was evaporated
  4. extractionthe residue worked up by extraction

出典と根拠

ORDレコード
ord-da13a31426dc4cfcb1856c485413f595
出典データセット
uspto-grants-1997_04
特許番号
US05616610

反応ノート

読み込み中…