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benzyl 3-(chlorocarbonyl)tetrahydro-1(2H)-pyridinecarboxylate → (+/-)-Benzyl 3-(6-methoxy-2-methyl-1-oxo-4-phenyl-1,2-dihydroisoquinolin-3-yl)piperidine-1-carboxylate

HRID 17866
Notes
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Reaction equation

HRID 17866 reaction equation
C(O)(C)C.C(=O)=O.[CH3:8][O:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([NH:16][CH3:17])=[O:15])=[C:12]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:11]=1.C([Li])(CC)C.[CH2:32]([O:39][C:40]([N:42]1[CH2:47][CH2:46][CH2:45][CH:44]([C:48](Cl)=O)[CH2:43]1)=[O:41])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>O1CCCC1.CCOC(C)=O.CCCCCC>[CH3:8][O:9][C:10]1[CH:11]=[C:12]2[C:13](=[CH:18][CH:19]=1)[C:14](=[O:15])[N:16]([CH3:17])[C:48]([CH:44]1[CH2:45][CH2:46][CH2:47][N:42]([C:40]([O:39][CH2:32][C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)=[O:41])[CH2:43]1)=[C:20]2[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 2776575benzyl 3-(chlorocarbonyl)tetrahydro-1(2H)-pyridinecarboxylateHCID 225559272-Benzyl-4-methoxy-N-methylbenzamideHCID 86586944Isopropanol carbon dioxideHCID 178418400CID 53628100

Product 1

HCID 11397523(+/-)-Benzyl 3-(6-methoxy-2-methyl-1-oxo-4-phenyl-1,2-dihydroisoquinolin-3-yl)piperidine-1-carboxylate

Reagents, catalysts & solvents

2
HCID 8028TetrahydrofuranSolvent2×HCID 21226206Ethyl acetate hexaneSolvent

Procedure

To an isopropanol-dry ice cooled solution of 4-methoxy-N-methyl-2-(phenylmethyl)benzamide (500 mg, 1.96 mmol) in tetrahydrofuran (90 mL) was added dropwise a 1.3 M solution of sec-butyllithium (3.09 mL, 4.02 mmol). After 15 min. a solution of (±)-benzyl-3-(chlorocarbonyl)piperidine-1-carboxylate (550 mg, 1.96 mmol) in tetrahydrofuran (10 mL) was added. After 0.5 hours the contents of the reaction flask were first warmed to room temperature and then the solvent was removed in vacuo. The resulting mixture was treated with 1 M hydrochloric acid and extracted (3×) with ethyl acetate. The combined organic extracts were dried with anhydrous sodium sulfate, filtered and evaporated in vacuo. Trifluoroacetic acid (1 mL) was added and the resulting solution stirred 10 min. The reaction was quenched with water and made basic with saturated sodium bicarbonate. Extracted with ethyl acetate (3×), dried combined organic extracts with anhydrous sodium sulfate and removed solvent in vacuo to give a white foam. Flash column chromatography (50% EtOAc/hexane) afforded the title compound as a white foam. Proton NMR for the product was consistent with the titled compound. ESI+MS: 483.3 [M+H]+.

Workup

  1. customthe solvent was removed in vacuo
  2. additionThe resulting mixture was treated with 1 M hydrochloric acid
  3. extractionextracted (3×) with ethyl acetate
  4. dry with materialThe combined organic extracts were dried with anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. additionTrifluoroacetic acid (1 mL) was added
  8. customThe reaction was quenched with water
  9. extractionExtracted with ethyl acetate (3×)
  10. customdried
  11. customremoved solvent in vacuo
  12. customto give a white foam

Sources & evidence

ORD record
ord-9cebfc88978d45a485a97533adabc742
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07741322B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes