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

HRID 926161

Reaktionsgleichung

Reaktionsgleichung von HRID 926161
[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

Komponenten

8

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24193Titanium TetrachlorideKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-a3138a8544fd4d748c06521b08de24f7
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09284323B2

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