Sodium borohydride → (3-(4-(4-Chlorophenyl)cyclohexyl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)methanol

HRID 1506378Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1506378
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][CH:11]([C:14]3[O:18][N:17]=[C:16]4[C:19]5[C:24]([CH2:25][CH2:26][C:15]=34)=[CH:23][C:22]([CH:27]([OH:30])CO)=[CH:21][CH:20]=5)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.I([O-])(=O)(=O)=O.[Na+].[BH4-].[Na+]>CO.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:13][CH2:12][CH:11]([C:14]3[O:18][N:17]=[C:16]4[C:19]5[C:24]([CH2:25][CH2:26][C:15]=34)=[CH:23][C:22]([CH2:27][OH:30])=[CH:21][CH:20]=5)[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 4311764Sodium borohydrideHCID 23667635Sodium periodateHCID 671720721-(3-(4-(4-Chlorophenyl)cyclohexyl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)ethane-1,2-diol

Produkt 1

HCID 67168754(3-(4-(4-Chlorophenyl)cyclohexyl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 1-(3-(4-(4-chlorophenyl)cyclohexyl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)ethane-1,2-diol (Preparation 27C, 0.05 g, 0.118 mmol) in methanol (1.0 mL) at 0° C. was added a solution of sodium periodate (0.030 g, 0.142 mmol) in water (1.0 mL) dropwise. The white heterogeneous reaction mixture was stirred for 40 mins. at the same temperature and then partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhyd. sodium sulfate and concentrated. The residue was taken in methanol (2 mL) and treated with sodium borohydride (5.35 mg, 0.142 mmol) at room temperature. After 1 h, the reaction was quenched with saturated. aq. sodium bicarbonate. After stirring for 30 min, the reaction mixture was partitioned between ethyl acetate and water. The ethyl acetate layer was washed with brine, dried over anhyd. magnesium sulfate and concentrated to yield (3-(4-(4-chlorophenyl)cyclohexyl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)methanol.

Aufarbeitung

  1. customThe white heterogeneous reaction mixture
  2. customat the same temperature and then partitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. customdried over anhyd
  5. concentrationsodium sulfate and concentrated
  6. waitAfter 1 h
  7. customthe reaction was quenched with saturated
  8. stirringAfter stirring for 30 min
  9. customthe reaction mixture was partitioned between ethyl acetate and water
  10. washThe ethyl acetate layer was washed with brine
  11. customdried over anhyd
  12. concentrationmagnesium sulfate and concentrated

Quellen und Nachweise

ORD-Eintrag
ord-791adea887e040d690e54bd889b7c506
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09216972B2

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