反応 #51617

反応方程式

HCl

cyclohexanone

borane

NaOH

pyridine

3-amino-6,7-dimethoxy-quinoline hydrochloride

NaOMe

→

light-yellow solid

収率 57.0%

3-Aminocyclohexyl-6,7-dimethoxy-quinoline

収率 57.0%

溶媒

MeOH

反応条件

後処理

1. 1
   workup.STIRRINGThe mixture is stirred for 4.5 h
2. 2
   workup.STIRRINGThe reaction mixture is stirred 45 min.
3. 3
   その他The mix is partitioned between EtOAC and H2O
4. 4
   洗浄the aqueous layer is washed with EtOAc (2×)
5. 5
   洗浄The combined organic layers are washed with brine, (1×),
6. 6
   乾燥dried (MgSO4)
7. 7
   その他chromatographed (50% EtOAc/hexanes)
8. 8
   その他recrystallized from EtOAc/hexanes

実験手順

To a MeOH (3 mL) solution of 4 Å powdered molecular sieves (0.11 g) under argon is added 3-amino-6,7-dimethoxy-quinoline hydrochloride (0.17 g, 0.68 mmol) and NaOMe (0.039 g, 0.71 mmol). The reaction mixture is stirred at room temperature for 30 min., and cyclohexanone (0.074 mL, 0.71 mmol), then pyridine.borane (0.072 mL, 0.071 mmol) are added portionwise. The mixture is stirred for 4.5 h, then 5N HCl (1.4 mL, 6.8 mmol) is added portionwise. The reaction mixture is stirred 45 min., then made strongly basic with 5N NaOH. The mix is partitioned between EtOAC and H2O, and the aqueous layer is washed with EtOAc (2×). The combined organic layers are washed with brine, (1×), dried (MgSO4), chromatographed (50% EtOAc/hexanes), and recrystallized from EtOAc/hexanes to obtain 0.112 g light-yellow solid in 57% yield (m.p. 164-165). Anal. calcd for C17H22N2O2: C, 71.30; H, 7.74; N, 9.78. Found: C, 71.45; H, 7.49; N, 9.80.

出典