Acetic Acid → (S)-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl) 2-(7-bromo-1-hydroxy-3-methylnaphthalen-2-yl)-2-hydroxyacetate

HRID 926161ノート

反応式

HRID 926161 の反応式
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH3:13])[CH:8]=[C:9]2[OH:12])=[CH:4][CH:3]=1.O.[C:15]([O:19][CH:20]1[CH:25]([CH:26]([CH3:28])[CH3:27])[CH2:24][CH2:23][C@@H:22]([CH3:29])[CH2:21]1)(=[O:18])[CH:16]=[O:17].C(O)(=O)C.C(#N)C>ClCCl.[Ti](Cl)(Cl)(Cl)Cl.O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH3:13])[C:8]([C@H:16]([OH:17])[C:15]([O:19][C@@H:20]3[CH2:21][C@H:22]([CH3:29])[CH2:23][CH2:24][C@H:25]3[CH:26]([CH3:28])[CH3:27])=[O:18])=[C:9]2[OH:12])=[CH:4][CH:3]=1

参加物

8

反応物 4

HCID 176Acetic AcidHCID 6342AcetonitrileHCID 44593838(1R)-(-)-Menthyl glyoxylate hydrateHCID 671262827-Bromo-3-methylnaphthalen-1-ol

生成物 1

HCID 118023859(S)-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl) 2-(7-bromo-1-hydroxy-3-methylnaphthalen-2-yl)-2-hydroxyacetate

試薬・触媒・溶媒 3

HCID 24193Titanium Tetrachloride触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
40 °C

実験手順

To a solution of 7-bromo-3-methylnaphthalen-1-ol (11.8 g, 50.0 mmol) in dichloromethane (25 mL) at −40° C. was added a 1 M titanium(IV) chloride solution in dichloromethane (50.0 mL, 50.0 mmol) and stirred for 20 min. (1R)-(−)-Menthyl glyoxylate hydrate (12.1 g, 52.5 mmol) was added over 15 minutes in small portions as a solid and stirred for 1 hour at 40° C. Then acetic acid (20 mL) and acetonitrile (60 mL) were added while cold. Water (200 mL) was added and the resulting solution was stirred at room temperature for 30 min. The layers were separated, and the aqueous layer was extracted with CH2Cl2. The combined organic layer was dried, filtered, concentrated. The crude material, which was about 8:1 d.r., was taken on without further purification.

後処理

  1. additionwas added over 15 minutes in small portions as a solid
  2. stirringthe resulting solution was stirred at room temperature for 30 min
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with CH2Cl2
  5. customThe combined organic layer was dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custom1 d
  9. custom, was taken on without further purification

出典と根拠

ORDレコード
ord-a3138a8544fd4d748c06521b08de24f7
出典データセット
uspto-grants-2016_03
特許番号
US09284323B2

反応ノート

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