Aluminium lithium hydride → 5,5-Diethoxy-2-piperidinemethanol

HRID 60829Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([O:9][C:10]1([O:21][CH2:22][CH3:23])[CH2:15][NH:14][CH:13]([C:16](OCC)=[O:17])[CH2:12][CH2:11]1)[CH3:8]>C1COCC1>[CH2:22]([O:21][C:10]1([O:9][CH2:7][CH3:8])[CH2:15][NH:14][CH:13]([CH2:16][OH:17])[CH2:12][CH2:11]1)[CH3:23]

Participants

Conditions

Temperature: 70 °C

Procedure

A suspension of LAH (0.47 g, 12.25 mmol) in anhydrous THF (5 mL) was added a solution of ethyl 5,5-diethoxypiperidine-2-carboxylate (0.6 g, 2.45 mmol) in anhydrous THF (5 mL) dropwise at rt. The resulting mixture was refluxed at 70° C. for overnight. The reaction mixture was cooled down to 0° C. and quenched sequentially with water (0.47 g), 15% NaOH (0.47 g) and water (1.41 g). The resulting suspension was stirred at rt for 1 h and filtered. The filtrate was concentrated in vacuo to give desired rac-(5,5-diethoxypiperidin-2-yl)methanol in 95% yield as colorless oil. 1H NMR (CDCl3, 400 MHz) δ 3.54-3.32 (m, 6H), 3.11-3.04 (m, 1H), 2.56-2.46 (m, 2H), 2.05-2.00 (m, 1H), 1.52-1.23 (m, 3H), 1.15-1.07 (m, 6H).

Workup

temperatureThe reaction mixture was cooled down to 0° C.
customquenched sequentially with water (0.47 g), 15% NaOH (0.47 g) and water (1.41 g)
filtrationfiltered
concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-d0c96c15ec804e5a936bfdb6cea39d58
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440982B2

Reaction notes

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