Diisobutylaluminumhydride → tert-Butyl 3-(hydroxymethyl)-3-(4-methylbenzyl)piperidine-1-carboxylate

HRID 1860642Notes

Reaction equation

[H-].C([Al+]CC(C)C)C(C)C.[CH3:11][C:12]1[CH:36]=[CH:35][C:15]([CH2:16][C:17]2([C:30](OCC)=[O:31])[CH2:22][CH2:21][CH2:20][N:19]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:18]2)=[CH:14][CH:13]=1>C1COCC1.CCOCC>[OH:31][CH2:30][C:17]1([CH2:16][C:15]2[CH:35]=[CH:36][C:12]([CH3:11])=[CH:13][CH:14]=2)[CH2:22][CH2:21][CH2:20][N:19]([C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24])[CH2:18]1

Participants

Conditions

Temperature: -20 °C

Procedure

A solution of diisobutylaluminum hydride (12.0 ml, 12.0 mmol, 1M in THF) was added dropwise to a solution of the product from STEP 2 (1.5 g, 6.0 mmol) in 15 ml THF at −20° C. The resulting mixture was stirred at −20° C. for 20 min and allowed to warm to room temperature. After 3 h, the reaction was diluted with ether (70 ml) and washed with 50 ml of aqueous 1M tartaric acid. The organic extracts were dried with MgSO4, filtered and concentrated. The residue was purified by chromatography (SiO2, ethyl acetate/hexane=1/3) to afford 0.58 g of a viscous. The 1H NMR spectrum of the product was consistent for the proposed structure.

Workup

temperatureto warm to room temperature
waitAfter 3 h
washwashed with 50 ml of aqueous 1M tartaric acid
dry with materialThe organic extracts were dried with MgSO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by chromatography (SiO2, ethyl acetate/hexane=1/3)
customto afford 0.58 g of a viscous

Sources & evidence

ORD record: ord-765d19f4b0b04b8bb67f0a7dd9a7a847
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06531494B1

Reaction notes

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