Triethylamine → HCID 178469204, compound

HRID 525464Notes

Reaction equation

HRID 525464 reaction equation
C(N(CC)CC)C.[C:8]([C@H:12]1[CH2:17][CH2:16][C@H:15]([O:18][C:19]2[CH:28]=[C:27]3[C:22]([CH:23]=[C:24]([CH:29]=O)[N:25]=[CH:26]3)=[CH:21][CH:20]=2)[CH2:14][CH2:13]1)([CH3:11])([CH3:10])[CH3:9].[NH:31]1[CH2:36][CH2:35][CH:34]([C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH2:33][CH2:32]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(Cl)Cl>[CH2:40]([O:39][C:37]([CH:34]1[CH2:35][CH2:36][N:31]([CH2:29][C:24]2[N:25]=[CH:26][C:21]3[C:22]([CH:23]=2)=[CH:27][CH:28]=[C:19]([O:18][C@H:15]2[CH2:14][CH2:13][C@H:12]([C:8]([CH3:11])([CH3:9])[CH3:10])[CH2:17][CH2:16]2)[CH:20]=3)[CH2:32][CH2:33]1)=[O:38])[CH3:41]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 70770Ethyl 4-piperidinecarboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 178445791HCID 178445791, compound

Product 1

HCID 178469204HCID 178469204, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

Triethylamine (65 μL, 0.47 mmol) was added to a solution of 7-(trans-4-tert-Butyl-cyclohexyloxy)-isoquinoline-3-carbaldehyde (0.106 g, 0.340 mmol) and Ethyl piperidine-4-carboxylate (79 mg, 0.50 mmol) in 1,2-Dichloroethane (5.00 mL) and the mixture was stirred for 1 hour at room temperature. Sodium triacetoxyborohydride (0.101 g, 0.476 mmol) was then added and stirring was continued for 2 hours. The reaction was diluted in methylene chloride and washed with saturated aqueous sodium bicarbonate. The organic phase was dried over magnesium sulfate, filtered, evaporated. The residue was taken up in methylene chloride and silica gel was added. The solvent was removed by evaporation and the residue purified by silica gel chromatography. 101 mg (66%) isolated. ESI-MS (M+H+): 453.10.

Workup

  1. stirringstirring
  2. waitwas continued for 2 hours
  3. washwashed with saturated aqueous sodium bicarbonate
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. additionsilica gel was added
  8. customThe solvent was removed by evaporation
  9. customthe residue purified by silica gel chromatography
  10. custom101 mg (66%) isolated

Sources & evidence

ORD record
ord-9171d36566f241139d8311e6ec15dd73
Source dataset
uspto-grants-2016_05
Patent number
US09340527B2

Reaction notes

Loading…