Diisopropylamine → HCID 66598832, compound

HRID 447233Notes

Reaction equation

HRID 447233 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[CH3:13][O:14][C:15](=[O:30])[CH2:16][CH:17]1[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]1.[N+:31]([C:34]1[CH:41]=[CH:40][CH:39]=[CH:38][C:35]=1[CH:36]=[O:37])([O-:33])=[O:32]>O1CCCC1>[C:26]([O:25][C:23]([N:20]1[CH2:19][CH2:18][CH:17]([CH:16]([C:15]([O:14][CH3:13])=[O:30])[CH:36]([OH:37])[C:35]2[CH:38]=[CH:39][CH:40]=[CH:41][C:34]=2[N+:31]([O-:33])=[O:32])[CH2:22][CH2:21]1)=[O:24])([CH3:27])([CH3:29])[CH3:28]

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 111012-NitrobenzaldehydeHCID 1514280tert-Butyl 4-(2-methoxy-2-oxoethyl)piperidine-1-carboxylateHCID 178418339Butyllithium

Product 1

HCID 66598832HCID 66598832, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-78 °C

Procedure

N,N-diisopropylamine (4.40 mL, 31.3 mmoles) was dissolved in tetrahydrofuran (50 mL). The mixture was cooled to −78° C. Butyllithium (2.5 M in hexanes, 12.4 mL, 31 mmoles) was added dropwise to the stirred solution. After stirring at −78° C. for 30 min, a solution of tert-butyl 4-(2-methoxy-2-oxoethyl)piperidine-1-carboxylate (6.65 g, 25.8 mmoles) in tetrahydrofuran (15 mL) was added dropwise to the mixture. Stirring was continued at −78° C. for 1 h. A solution of 2-nitrobenzaldehyde (3.90 g, 25.8 mmoles) in tetrahydrofuran (20 mL) was then added to the mixture dropwise, and then stirring was continued at −78° C. for a further 2.5 h. The reaction was quenched with cold aqueous ammonium chloride and then diluted with water. The mixture was extracted twice with ethyl acetate and the aqueous phase was discarded. The material was dried (magnesium sulfate) filtered, and concentrated to dryness. Silica gel chromatography afforded the desired product in 94% yield as light yellow foam. MS m/e (M-C4H8+H)+=353.1.

Workup

  1. stirringStirring
  2. waitwas continued at −78° C. for 1 h
  3. stirringstirring
  4. waitwas continued at −78° C. for a further 2.5 h
  5. customThe reaction was quenched with cold aqueous ammonium chloride
  6. additiondiluted with water
  7. extractionThe mixture was extracted twice with ethyl acetate
  8. dry with materialThe material was dried (magnesium sulfate)
  9. filtrationfiltered
  10. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-299b3dcb0b30426db32b0b5d567a7c15
Source dataset
uspto-grants-2013_07
Patent number
US08481546B2

Reaction notes

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