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Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → ethyl 3-(N-benzyloxycarbonylpiperid-2-yl)-2-propenoate

HRID 744143
Notes
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Reaction equation

HRID 744143 reaction equation
[C:1]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[CH:16]=O)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[C:18]([N:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH:29]1[CH:34]=O)([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19].[C:36]([CH:41]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:38][CH2:39][CH3:40])=[O:37]>O1CCCC1>[CH2:4]([O:3][C:1]([N:11]1[CH2:15][CH2:14][CH:13]=[C:12]1[CH:16]=[CH:41][C:36]([O:38][CH2:39][CH3:40])=[O:37])=[O:2])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1.[CH2:21]([O:20][C:18]([N:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH:29]1[CH:34]=[CH:41][C:36]([O:38][CH2:39][CH3:40])=[O:37])=[O:19])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 11064320Benzyl 2-formylpyrrolidine-1-carboxylateHCID 18375697Benzyl 2-formylpiperidine-1-carboxylate

Product 2

HCID 54132542ethyl 3-(N-benzyloxycarbonylpiperid-2-yl)-2-propenoateHCID 54411454HCID 54411454, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of N-carbobenzyloxypyrrolidine-2-carboxaldehyde or N-carbobenzyloxypiperidine-2-carboxaldehyde (5.00 mmol) [S. Kiyooka, et al., J. Org, Chem., 5409 (1989) and Y. Hamada, et al., Chem. Pharm. Bull., 1921 (1982)] in anhydrous tetrahydrofuran at -78° C. was added (carbethoxymethylene) triphenylphosphorane (2.09 g, 6.00 mmol. 1.2 eq) as a solid portionwise. The resulting reaction mixture was stirred at room temperature under nitrogen for 2 hours, and then heated at reflux under nitrogen for 1 hour. The reaction mixture was evaporated under reduced pressure and the residue was column chromatograPhed using silica gel (approximately 100 g) and elution with 20% diethyl ether in hexanes afforded either ethyl 3-(N-benzyloxycarbonylpyrrolin-2-yl)-2-propenoate or ethyl 3-(N-benzyloxycarbonylpiperid-2-yl)-2-propenoate.

Workup

  1. customThe resulting reaction mixture
  2. temperatureheated
  3. temperatureat reflux under nitrogen for 1 hour
  4. customThe reaction mixture was evaporated under reduced pressure
  5. customchromatograPhed
  6. washsilica gel (approximately 100 g) and elution with 20% diethyl ether in hexanes

Sources & evidence

ORD record
ord-f892b6de320b4bab810df2c636119ef4
Source dataset
uspto-grants-1996_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05559129

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes