Diethyl Ether → HCID 67722036, compound

HRID 52539Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1([C:24](OC)=[O:25])[CH2:17][CH2:16][CH:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH2:14]2)[N:9]1C(=O)C(F)(F)F.[OH-].[Na+].C(OCC)C>C1COCC1>[OH:25][CH2:24][C:8]1([CH3:7])[CH2:17][CH2:16][CH:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH2:14]2)[NH:9]1

Participants

Conditions

Temperature: 60 °C

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).

Workup

temperaturewhile the reaction temperature was maintained at 40°~45° C
customThe organic layer was separated
washwashed with brine three times
dry with materialdried over magnesium sulfate
concentrationconcentrated
customThe residue was purified by silica gel column chromatography with 3:1 hexane/ethyl acetate

Sources & evidence

ORD record: ord-2ba62142ebeb485499b1dab7f77c6fd9
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05616586

Reaction notes

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