Piperidine → HCID 69516063, compound

HRID 458460Notes

Reaction equation

HRID 458460 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][C:6]([C@@H:8]1[CH2:12][CH2:11][CH2:10][N:9]1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=O)[CH3:2].[NH2:21]/[C:22](/[CH2:29][CH2:30][C:31]([F:34])([F:33])[F:32])=[CH:23]\[C:24]([O:26][CH2:27][CH3:28])=[O:25].[CH:35]([C:37]1[CH:45]=[CH:44][C:40]([C:41]([OH:43])=[O:42])=[CH:39][CH:38]=1)=O.N1CCCCC1>C1(C)C=CC=CC=1>[C:16]([O:15][C:13]([N:9]1[CH2:10][CH2:11][CH2:12][C@H:8]1[C:6]1[NH:21][C:22]([CH2:29][CH2:30][C:31]([F:32])([F:33])[F:34])=[C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:35]([C:37]2[CH:45]=[CH:44][C:40]([C:41]([OH:43])=[O:42])=[CH:39][CH:38]=2)[C:5]=1[C:4]([O:3][CH2:1][CH3:2])=[O:20])=[O:14])([CH3:19])([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 8082PiperidineHCID 120884-Formylbenzoic acidHCID 57407385(S)-1-Boc-2-(3-ethoxy-3-oxopropanoyl)pyrrolidineHCID 86598173HCID 86598173, compound

Product 1

HCID 69516063HCID 69516063, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of tert-Butyl (2S)-2-(3-ethoxy-3-oxopropanoyl)-1-pyrrolidinecarboxylate (1.35 g, 4.74 mmol) in 30 mL of toluene, ethyl (2Z)-3-amino-6,6,6-trifluoro-2-hexenoate (1.0 g, 4.74 mmol) was added followed by 4-formylbenzoic acid (0.711 g, 4.74 mmol) and piperidine (0.202 g, 2.37 mmol). The reaction was allowed to reflux for 3 h. The crude mixture was concentrated and carried on without purification.

Workup

  1. temperatureto reflux for 3 h
  2. concentrationThe crude mixture was concentrated
  3. customcarried on without purification

Sources & evidence

ORD record
ord-588df96fc7cb4e24b5a3397d96368f75
Source dataset
uspto-grants-2007_03
Patent number
US07189851B2

Reaction notes

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