4-tert-Butylcyclohexylamine → HCID 178468863, Verbindung

HRID 230019

Reaktionsgleichung

Reaktionsgleichung von HRID 230019
[C:1]([C:4]1[CH:14]=[CH:13][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][CH:5]=1)(=O)[CH3:2].[C:15]([CH:19]1[CH2:24][CH2:23][CH:22]([NH2:25])[CH2:21][CH2:20]1)([CH3:18])([CH3:17])[CH3:16].[BH4-].[Na+]>C(O)C.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[C:15]([C@H:19]1[CH2:20][CH2:21][C@H:22]([NH:25][CH:1]([C:4]2[CH:14]=[CH:13][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][CH:5]=2)[CH3:2])[CH2:23][CH2:24]1)([CH3:18])([CH3:16])[CH3:17]

Komponenten

6

Edukt 3

HCID 793964-tert-ButylcyclohexylamineHCID 600911Ethyl 4-acetylbenzoateHCID 4311764Sodium borohydride

Produkt 1

HCID 178468863HCID 178468863, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11026Titanium isopropoxideKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of ethyl 4-acetylbenzoate (3.00 g, 15.6 mmol), titanium (IV) isopropoxide (9.30 mL, 31.2 mmol), 4-tert-butylcyclohexyl amine (4.85 g, 31.2 mmol) in absolute ethanol (100 mL) was stirred under nitrogen at room temperature for 10 h. Sodium borohydride (0.88 g, 23.4 mmol) was then added and the resulting mixture was stirred for an additional 8 h at room temperature. The reaction was quenched by pouring into aqueous ammonia (2N, 225 mL). The resulting inorganic precipitate was filtered off and washed with dichloromethane (100 mL). The organic layer was separated and the remaining aqueous layer was extracted once with dichloromethane (100 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated. Chromatography (20% EtOAc in Hexane) afforded ethyl 4-{1-[(trans-4-tert-butylcyclohexyl)amino]ethyl}benzoate. HPLC/MS: m/z=332.3 (M+1), Rt=2.74 min. 1HNMR (500 MHz, CDCl3): δ 8.01 (2H, d, J=8.1 Hz), 7.38 (2H, d, J=8.0 Hz), 4.37 (2H, q, J=7.1 Hz), 4.02 (1H, q, J=6.6 Hz), 2.18-2.06 (2H, m), 1.77-1.67 (4H, m), 1.39 (3H, t, J=7.1 Hz), 1.32 (3H, d, J=6.5 Hz), 1.22 (1H, br s), 1.09-0.85 (4H, m), 0.79 (9H, s).

Aufarbeitung

  1. stirringthe resulting mixture was stirred for an additional 8 h at room temperature
  2. customThe reaction was quenched
  3. additionby pouring into aqueous ammonia (2N, 225 mL)
  4. filtrationThe resulting inorganic precipitate was filtered off
  5. washwashed with dichloromethane (100 mL)
  6. customThe organic layer was separated
  7. extractionthe remaining aqueous layer was extracted once with dichloromethane (100 mL)
  8. dry with materialThe combined organic extracts were dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ab23a8b3691249bdbcf244877fbb3fd8
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07563815B2

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