Ethyl 4-piperidinecarboxylate → HCID 70147112, compound

HRID 1815513Notes

Reaction equation

HRID 1815513 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9][C:10]1[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[C:18](O)=[O:19])=[C:12]([C:21]([F:24])([F:23])[F:22])[C:11]=1[Cl:25].[NH:26]1[CH2:36][CH2:35][CH:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:28][CH2:27]1.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9][C:10]1[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[C:18]([N:26]2[CH2:27][CH2:28][CH:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:35][CH2:36]2)=[O:19])=[C:12]([C:21]([F:23])([F:22])[F:24])[C:11]=1[Cl:25]

Participants

5

Reactant 3

HCID 70770Ethyl 4-piperidinecarboxylateHCID 81531DiisopropylethylamineHCID 11811176HCID 11811176, compound

Product 1

HCID 70147112HCID 70147112, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the acyl chloride (37 mg, 0.1 mmol) prepared from the compound of Example 351B, as a solution in CH2Cl2 was added 1.2 eq. of ethyl isonipecotate and 1.2 eq. of Hunig's base. The mixture was stirred at room temperature for 20 min., ˜90% of the solvent was removed in vacuo, and the resultant solution was loaded on a silica column to elute with hexane and EtOAc (3:2) to give 51 mg (98%) of the title compound. 1H-NMR (CDCl3, 300 MHz) δ 1.25 (t, J=7.5 Hz, 3H), 1.65-1.78 (m, 2H), 1.92-2.02 (br, 2H), 2.51-2.60 (m, 1H), 2.93-3.24 (br, 2H), 3.82 (s, 3H), 3.88-3.96 (m, 1H), 4.15 (q,J=7.5 Hz, 2H), 4.40-4.50 (br, 1H), 6.48 (d, J=l15 Hz, 1H), 6.72 (d, J=9 Hz, 1H), 7.02 (d, J=7.5 Hz, 2H), 7.12 (d, J=9 Hz, 1H), 7.49 (t, J=9 Hz, (qq, J=4.5 Hz, 1H). MS (DCI/NH3) m/e 528 (M+H)+.

Workup

  1. custom˜90% of the solvent was removed in vacuo
  2. washto elute with hexane and EtOAc (3:2)

Sources & evidence

ORD record
ord-d94979f8c03c498cbc842b68203948de
Source dataset
uspto-grants-2005_04
Patent number
US06878700B1

Reaction notes

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