Diisobutylaluminumhydride → HCID 57937448, compound

HRID 1435135Notes

Reaction equation

[C:1]([C:4]1[CH:9]=[C:8]([O:10][CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)[CH:7]=[CH:6][N:5]=1)(=[O:3])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C>C(Cl)Cl>[OH:3][CH:1]([C:4]1[CH:9]=[C:8]([O:10][CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[CH2:13][CH2:12]2)[CH:7]=[CH:6][N:5]=1)[CH3:2]

Participants

Conditions

Temperature: -78 °C

Procedure

1,1-Dimethylethyl 4-[(2-acetyl-4-pyridinyl)oxy]-1-piperidinecarboxylate (1.62 g, 5.06 mmol) was dissolved in 50.0 mL of anhydrous DCM and the solution cooled to −78° C. Diisobutylaluminumhydride (15.2 ml, 15.2 mmol, 1.0M solution in hexanes) was added dropwise over 15 min and the reaction continued to be stirred at −78° C. for 1.5 h. The reaction was quenched with 50 mL of saturated sodium potassium tartrate solution, warmed to rt and stirred overnight. The organics were separated, washed with brine and dried over MgSO4. The crude was purified via silica gel chromatography to give 0.962 g (59% yield) of the title compound, 1H NMR (300 MHz, Chloroform-d) δ 8.40 (d, J=5.8 Hz, 1H), 6.83 (d, J=2.4 Hz, 1H), 6.77 (dd, J=5.8, 2.4 Hz, 1H), 4.82-4.97 (m, J=6.5, 6.5 Hz, 1H), 4.51-4.74 (m, 1H), 3.62-3.83 (m, 2H), 3.29-3.53 (m, 2H), 1.90-2.08 (m, 2H), 1.66-1.90 (m, 2H), 1.55 (d, J=6.5 Hz, 3H), 1.52 (s, 9H).

Workup

customThe reaction was quenched with 50 mL of saturated sodium potassium tartrate solution
temperaturewarmed to rt
stirringstirred overnight
customThe organics were separated
washwashed with brine
dry with materialdried over MgSO4
customThe crude was purified via silica gel chromatography

Sources & evidence

ORD record: ord-63c26c14ef5a42f6adccf6ca84033e72
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07615643B2

Reaction notes

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