Diisobutylaluminum hydride → HCID 86708249, compound

HRID 534191Notes

Reaction equation

HRID 534191 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]1[CH2:12][CH2:11][N:10]([CH2:13][C:14](OCC)=[O:15])[CH2:9][CH2:8]1.CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]1[CH2:8][CH2:9][N:10]([CH2:13][CH:14]=[O:15])[CH2:11][CH2:12]1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 68385283HCID 68385283, compound

Product 1

HCID 86708249HCID 86708249, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of ethyl 2-(4-(pyridin-2-yl)piperidin-1-yl)acetate (600 mg, 2.416 mmol) in toluene (20 mL) was added DIBAL-H (3.62 mL, 3.62 mmol, 1M in toluene) at −78° C. and stirred for 3 h at −78° C. The reaction mixture was quenched with methanol (0.5 mL) and then brine (10 mL) was added. The reaction mixture was filtered through celite and the filtrate was dried over sodium sulphate and concentrated under reduced pressure to afford 2-(4-(pyridin-2-yl)piperidin-1-yl)acetaldehyde (400 mg, 77% yield) as pale yellow solid. LCMS (ES) m/e 205.16 (M+H)+.

Workup

  1. customThe reaction mixture was quenched with methanol (0.5 mL)
  2. additionbrine (10 mL) was added
  3. filtrationThe reaction mixture was filtered through celite
  4. dry with materialthe filtrate was dried over sodium sulphate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a18399f668bc4344b77e650faccd85fb
Source dataset
uspto-grants-2014_10
Patent number
US08853408B2

Reaction notes

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