Hydrochloric Acid → Tert-butyl 3-hydroxy-3-phenyl-3-(pyridin-2-yl)propionate

HRID 1296842

反応式

HRID 1296842 の反応式
C=C[C@@H]1[C@@H:8]2[CH2:9][C@H:10]([C@@H:11]([OH:22])[C:12]3[CH:13]=[CH:14]N=C4C=C[CH:19]=[CH:18][C:17]=34)[N:5]([CH2:6][CH2:7]2)C1.N1C=CC=C[CH:24]=1.[C:29]([C:37]1C=CC=CN=1)(=[O:36])[C:30]1C=CC=CC=1.Cl.[O:44]1CC[CH2:46][CH2:45]1>>[OH:22][C:11]([C:12]1[CH:17]=[CH:18][CH:19]=[CH:14][CH:13]=1)([C:10]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1)[CH2:46][C:45]([O:36][C:29]([CH3:30])([CH3:37])[CH3:24])=[O:44]

参加物

6

反応物 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 70382-BenzoylpyridineHCID 8028Tetrahydrofuran2 回HCID 90454Cinchonine

生成物 1

HCID 12150309Tert-butyl 3-hydroxy-3-phenyl-3-(pyridin-2-yl)propionate収率 98%

反応条件

温度
-40 °C

実験手順

Under argon atmosphere, cinchonine (440 mg, 1.0 mmol) was suspended in tetrahydrofuran (absolute, 2.0 mL), and to this suspension was added a Reformatsky reagent (0.5 M; 8.0 mL, 4.0 mmol) dropwise under ice-cooling. After stirring for 10 minutes, pyridine (0.30 mL, 2 mmol) was added thereto dropwise. After stirring for 20 minutes under ice-cooling, the mixture was cooled to −40° C. A solution of 2-benzoylpyridine (183 mg, 1.0 mmol) in tetrahydrofuran (absolute, 4.0 mL) was added dropwise over 10 minutes, and the mixture was stirred at −40° C. for 4 hours. To this reaction solution was added 1N HCl (20 mL), which was then extracted with ethyl acetate (20 mL×2). The extracted solution was washed successively with an aqueous saturated sodium bicarbonate solution and an aqueous saturated sodium chloride solution. After the organic layer was dried with sodium sulfate, the solvent was removed under reduced pressure. The residue was analyzed with high performance liquid chromatography. Consequently, the yield was 98% and the enantiomer excess was 90%.

後処理

  1. additionto this suspension was added a Reformatsky reagent (0.5 M; 8.0 mL, 4.0 mmol) dropwise under ice-
  2. temperaturecooling
  3. stirringAfter stirring for 20 minutes under ice-
  4. temperaturecooling
  5. stirringthe mixture was stirred at −40° C. for 4 hours
  6. extractionwas then extracted with ethyl acetate (20 mL×2)
  7. washThe extracted solution was washed successively with an aqueous saturated sodium bicarbonate solution
  8. dry with materialAfter the organic layer was dried with sodium sulfate
  9. customthe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-d943000762e2401eb571aa59046206f2
出典データセット
uspto-grants-2007_07
特許番号
US07247732B2

関連ノート

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