Reaction #80817

Reaction equation

diethyl ether

lithium aluminum hydride

2-methyl-N-trifluoroacetyl-2-methoxycarbonyltetrahydroquinoline

sodium hydroxide

→

2-hydroxymethyl-2-methyltetrahydroquinoline

Yield 95.0%

Solvents

THF

THF

THF

Conditions

Workup

1. 1
   Temperaturewhile the reaction temperature was maintained at 40°~45° C
2. 2
   OtherThe organic layer was separated
3. 3
   Washwashed with brine three times
4. 4
   Dryingdried over magnesium sulfate
5. 5
   Concentrationconcentrated
6. 6
   OtherThe residue was purified by silica gel column chromatography with 3:1 hexane/ethyl acetate

Procedure

To a suspension of lithium aluminum hydride (1.12 g, 29.5 mmol) in THF (10 mL) was added dropwise 2-methyl-N-trifluoroacetyl-2-methoxycarbonyltetrahydroquinoline (8.88 g, 29.5 mmol) in THF (90 mL) over 25 min, while the reaction temperature was maintained at 40°~45° C. The mixture was heated at 60° C. for 1 h and the excess reagent was decomposed by slow addition of aqueous THF at 0° C. Aqueous sodium hydroxide was added and stirred for 30 min followed by addition of diethyl ether. The organic layer was separated, washed with brine three times, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography with 3:1 hexane/ethyl acetate to give 4.97 g of 2-hydroxymethyl-2-methyltetrahydroquinoline (95%): 1H NMR (270 MHz, CDCl3) δ6.98 (m, 2H), 6.64 (td, 1H, J=7.3, 1 Hz), 3.73 (bs, 1H), 3.47 (s, 2H), 2.76 (m, 2H), 1.93 (bs, 1H), 1.86 (m, 1H), 1.61 (m, 1H), 1.19 (s, 3H).

Source