Diisopropylamine → HCID 67099363, compound

HRID 1868809Notes

Reaction equation

HRID 1868809 reaction equation
C([Li])CCC.C(NC(C)C)(C)C.[CH2:13]([N:20]1[CH2:25][CH2:24][C:23]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[C:37]#[CH:38])([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:22][CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl[C:40]([O:42][CH2:43][CH3:44])=[O:41]>C1COCC1.C(Cl)Cl.CO>[CH2:13]([N:20]1[CH2:21][CH2:22][C:23]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[C:37]#[C:38][C:40]([O:42][CH2:43][CH3:44])=[O:41])([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:24][CH2:25]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

8

Reactant 4

HCID 7912DiisopropylamineHCID 10928Ethyl chloroformateHCID 86629258HCID 86629258, compoundHCID 178418339Butyllithium

Product 1

HCID 67099363HCID 67099363, compoundYield 56.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

n-Butyllithium (0.76 mL, 1.9 mmol) was added to a stirred solution of diisopropylamine (0.28 mL, 2.0 mmol) in THF (20 mL, 244 mmol) at −78° C. The reaction mixture was then allowed to warm to ambient temperature for 5 minutes before it was cooled down to −78° C. Ethyl 1-benzyl-4-(2-ethynylphenyl)piperidine-4-carboxylate (0.22 g, 0.63 mmol) was then added dropwise as a solution in THF (20 mL, 244 mmol). After 15 minutes, ethyl chloroformate (0.19 mL, 2.0 mmol) in 5 mL of THF was added to the reaction. The resulting solution was allowed to warm to ambient temperature and then stirred for 30 minutes. MeOH (3 mL) was added, and the resulting mixture was concentrated in vacuo to give a bright-yellow oil. The residue was dissolved in DCM and purified by Isco HPLC (0-80% EtOAc/hexane) to give the title compound as a yellow oil (0.15 g). MS m/e=420 (M+H)+.

Workup

  1. temperaturewas cooled down to −78° C
  2. temperatureto warm to ambient temperature
  3. concentrationthe resulting mixture was concentrated in vacuo
  4. customto give a bright-yellow oil
  5. custompurified by Isco HPLC (0-80% EtOAc/hexane)

Sources & evidence

ORD record
ord-f1e03b7f490e4379a408e6488dc9d338
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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