4-tert-Butylcyclohexylamine → HCID 178468863, 화합물

HRID 230019

반응식

HRID 230019 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

HCID 178468863HCID 178468863, 화합물

시약·촉매·용매 2

HCID 11026Titanium isopropoxide촉매HCID 702Ethanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ab23a8b3691249bdbcf244877fbb3fd8
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07563815B2

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