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

HRID 926161

반응식

HRID 926161 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 24193Titanium Tetrachloride촉매HCID 962Water용매HCID 6344Dichloromethane용매2회

반응 조건

온도
40 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a3138a8544fd4d748c06521b08de24f7
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09284323B2

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