Triethylamine → HCID 131736295, compound

HRID 1053805Notes

Reaction equation

HRID 1053805 reaction equation
[NH2:1][C@H:2]1[C@H:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:6][CH2:5][N:4]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:3]1.CCN(CC)CC.[Br:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32](Cl)=[O:33]>C(Cl)Cl>[Br:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([NH:1][C@H:2]1[C@H:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:6][CH2:5][N:4]([C:13]([O:15][C:16]([CH3:18])([CH3:17])[CH3:19])=[O:14])[CH2:3]1)=[O:33]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5211735-Bromovaleryl chlorideHCID 131736294HCID 131736294, compound

Product 1

HCID 131736295HCID 131736295, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of trans-1-tert-butyl 4-ethyl 3-aminopiperidine-1,4-dicarboxylate 7 (2.5 g, 9.2 mmol, 1.0 equiv) in CH2Cl2 (50 mL), Et3N (2.5 mL, 18.4 mmol, 2.0 equiv) was added at rt. After the reaction solution was stirred at rt for 10 min, 5-bromovaleryl chloride (1.9 g, 9.6 mmol, 1.05 eq) was added. The reaction solution was stirred at rt for 2 h. The mixture was quenched with H2O (20 mL) and extracted with CH2Cl2 (50 mL×3). The organic layer was collected, concentrated in vacuo, and the residue was purified by column chromatography (silica, petroleum ether/EtOAc=1:1) to give (trans)-1-tert-butyl 4-ethyl 3-(5-bromopentanamido)piperidine-1,4-dicarboxylate 8 as yellow oil (3.2 g, yield: 80%). ESI-MS (M+H-56)+: 379.0. 1H NMR (400 MHz, CDCl3) δ: 5.99 (d, 1H), 4.39-4.38 (m, 1H), 4.15 (q, 2H), 3.79-3.74 (m, 1H), 3.66-3.60 (m, 1H), 3.41 (t, 2H), 3.30-3.26 (m, 1H), 3.21-3.14 (m, 1H), 2.78-2.74 (m, 1H), 2.19 (t, 2H), 1.99-1.85 (m, 3H), 1.80-1.72 (m, 3H), 1.45 (s, 9H), 1.27 (t, 3H).

Workup

  1. stirringThe reaction solution was stirred at rt for 2 h
  2. customThe mixture was quenched with H2O (20 mL)
  3. extractionextracted with CH2Cl2 (50 mL×3)
  4. customThe organic layer was collected
  5. concentrationconcentrated in vacuo
  6. customthe residue was purified by column chromatography (silica, petroleum ether/EtOAc=1:1)

Sources & evidence

ORD record
ord-6730173cee9440c0a681883257005b9e
Source dataset
uspto-grants-2016_07
Patent number
US09394277B2

Reaction notes

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