Acetic Acid → HCID 59264607, compound

HRID 646203Notes

Reaction equation

HRID 646203 reaction equation
[CH3:1][C:2]([N:9]1[CH2:14][CH2:13][C:12](=O)[CH2:11][CH2:10]1)([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].Cl.[F:17][C:18]([F:35])([F:34])[O:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][C:29]([CH2:32][NH2:33])=[CH:28][CH:27]=2)=[CH:22][CH:21]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>ClCCCl>[CH3:1][C:2]([N:9]1[CH2:14][CH2:13][CH:12]([NH:33][CH2:32][C:29]2[CH:30]=[CH:31][C:26]([C:23]3[CH:24]=[CH:25][C:20]([O:19][C:18]([F:17])([F:34])[F:35])=[CH:21][CH:22]=3)=[CH:27][CH:28]=2)[CH2:11][CH2:10]1)([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 10340Sodium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 22928457[1,1′-Biphenyl]-4-methanamine, 4′-(trifluoromethoxy)-, hydrochloride (1:1)HCID 59264612Ethyl 2-methyl-2-(4-oxo-1-piperidinyl)propanoate

Product 1

HCID 59264607HCID 59264607, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of ethyl 2-methyl-2-(4-oxo-1-piperidinyl)propanoate (Int. A4) (1.09 g, 1.2 equiv), ({4′-[(trifluoromethyl)oxy]-4-biphenylyl}methyl)amine hydrochloride (Int. A2) (1.28 g, 1.0 equiv), DCE (21 ml) and acetic acid (0.27 ml, 1.1 equiv) was stirred at room temperature under nitrogen. Sodium triacetoxyborohydride (1.42 g, 1.5 equiv) was added and stirring continued for 3 hours. Aqueous sodium carbonate (2M solution, excess) was added and stirred for 45 min, then the mixture was partitioned with a mixture of diethyl ether/THF and water. The organic extracts were backwashed with water and brine, and dried over sodium sulfate and evaporated in vacuo. The desired product was obtained as a light yellow solid (2.14 g) which was used without further purification.

Workup

  1. stirringstirring
  2. stirringstirred for 45 min
  3. customthe mixture was partitioned with a mixture of diethyl ether/THF and water
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-ffc425c6f3bb4d0e8ddd99681d0006c9
Source dataset
uspto-grants-2010_04
Patent number
US07705005B2

Reaction notes

Loading…