Isobutyraldehyde → HCID 11300027, compound

HRID 131189Notes

Reaction equation

HRID 131189 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH2:10][C:9]1=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N-]C(C)C)(C)C.[Li+].[CH:23](=[O:27])[CH:24]([CH3:26])[CH3:25]>O1CCCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([CH:23]([OH:27])[CH:24]([CH3:26])[CH3:25])[C:9]1=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6561IsobutyraldehydeHCID 2724682Lithium diisopropylamideHCID 122940874-Benzylmorpholin-3-one

Product 1

HCID 11300027HCID 11300027, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 2 (5.05 g, 26.4 mmol) in tetrahydrofuran (25 ml) at −78° C. under nitrogen was added lithium diisopropylamide (14.5 ml of a 2M solution, 29.0 mmol) dropwise over 40 minutes. The reaction mixture was stirred at the same temperature over 30 minutes after which time a solution of isobutyraldehyde (2.63 ml, 29.0 mmol) in tetrahydrofuran (15 ml) was added dropwise over 30 minutes. After one hour, the reaction mixture was allowed to warm to room temperature and quenched by addition of saturated ammonium chloride solution. Extraction with dichloromethane and drying over magnesium sulphate gave 53 as a mixture of diastereomers. Upon concentration in vacuo one diastereomer precipitated as a white solid (53a: 0.99 g). The remaining mother liquors were purified by column chromatography (30% ethyl acetate in hexane [v/v]) to give 53 (2.06 g). MW 263.34; C15H21NO3; LCMS (6 min method): m/z 286 [M+Na]+; RT=2.748.

Workup

  1. additionwas added dropwise over 30 minutes
  2. customquenched by addition of saturated ammonium chloride solution
  3. extractionExtraction with dichloromethane
  4. dry with materialdrying over magnesium sulphate

Sources & evidence

ORD record
ord-d9b56de4fdf94651b96639cdaf7e1b1b
Source dataset
uspto-grants-2008_06
Patent number
US07384941B2

Reaction notes

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