Acetic Acid → 7-amino-9a-butyl-8-chloro-6-fluoro-1,2,9,9a-tetrahydro-3H-fluoren-3-one

HRID 1372505ノート

反応式

HRID 1372505 の反応式
[NH2:1][C:2]1[C:3]([Cl:22])=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[C:7](=O)[C:6]([CH2:18][CH2:19][CH2:20][CH3:21])([CH2:13][CH2:14][C:15](=[O:17])[CH3:16])[CH2:5]2.C(O)(=O)C.N1CCCC1>C1(C)C=CC=CC=1>[NH2:1][C:2]1[C:3]([Cl:22])=[C:4]2[C:8]([C:7]3[C:6]([CH2:18][CH2:19][CH2:20][CH3:21])([CH2:5]2)[CH2:13][CH2:14][C:15](=[O:17])[CH:16]=3)=[CH:9][C:10]=1[F:11]

参加物

5

反応物 3

HCID 176Acetic AcidHCID 31268PyrrolidineHCID 210720055-Amino-2-butyl-4-chloro-6-fluoro-2-(3-oxobutyl)-1-indanone

生成物 1

HCID 210720137-amino-9a-butyl-8-chloro-6-fluoro-1,2,9,9a-tetrahydro-3H-fluoren-3-one収率 83%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
90 °C

実験手順

The crude diketone from step 7 (approx. 10.6 mmol) was dissolved in toluene (106 mL) and treated with acetic acid (0.606 mL, 10.6 mmol) and pyrrolidine (0.883 mL, 10.6 mmol). The resulting solution was stirred and heated in an oil bath at 90° C. for 3.5 hours. After cooling to room temperature, the mixture was filtered through a pad of silica gel and the product washed off with EtOAc. The filtrate and washings were concentrated under vacuum. The residue was purified by flash chromatography on a Biotage 40M KP-Sil column, eluting with 4:1 hexanes-EtOAc. The product containing fractions were evaporated under vacuum to provide 7-amino-9a-butyl-8-chloro-6-fluoro-1,2,9,9a-tetrahydro-3H-fluoren-3-one (2.7 g, 83%) as a yellow solid.

後処理

  1. temperatureAfter cooling to room temperature
  2. filtrationthe mixture was filtered through a pad of silica gel
  3. washthe product washed off with EtOAc
  4. concentrationThe filtrate and washings were concentrated under vacuum
  5. customThe residue was purified by flash chromatography on a Biotage 40M KP-Sil column
  6. washeluting with 4:1 hexanes-EtOAc
  7. additionThe product containing fractions
  8. customwere evaporated under vacuum

出典と根拠

ORDレコード
ord-f8f3ec3f1a4940b6a851ffda370e9718
出典データセット
uspto-grants-2007_01
特許番号
US07157604B2

反応ノート

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