4-tert-Butylcyclohexylamine → HCID 178468863, compound

HRID 230019

Reaction equation

HRID 230019 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

HCID 178468863HCID 178468863, compound

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 702EthanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-ab23a8b3691249bdbcf244877fbb3fd8
Source dataset
uspto-grants-2009_07
Patent number
US07563815B2

Linked notes

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