Acetic Acid → HCID 59264605, compound

HRID 646204Notes

Reaction equation

HRID 646204 reaction equation
[CH3:1][C:2]([N:11]1[CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]1)([CH3:10])[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[F:18][C:19]([F:35])([F:34])[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[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[CH3:1][C:2]([N:11]1[CH2:16][CH2:15][CH:14]([NH:33][CH2:32][C:29]2[CH:28]=[CH:27][C:26]([C:23]3[CH:24]=[CH:25][C:20]([C:19]([F:18])([F:34])[F:35])=[CH:21][CH:22]=3)=[CH:31][CH:30]=2)[CH2:13][CH2:12]1)([CH3:10])[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 10340Sodium CarbonateHCID 37291554-(4-TRIFLUOROMETHYLPHENYL)BENZYLAMINEHCID 5049666Sodium triacetoxyborohydrideHCID 59264611HCID 59264611, compound

Product 1

HCID 59264605HCID 59264605, compoundYield 57.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1,1-dimethylethyl 2-methyl-2-(4-oxo-1-piperidinyl)propanoate (Int. A6) (370 mg, 1.2 equiv), {[4′-(trifluoromethyl)-4-biphenylyl]methyl}amine (Int. A1) (397 mg, 1 equiv), sodium triacetoxyborohydride (400 mg, 1.5 equiv), DCM (10 ml) and acetic acid (0.076 ml, 1 equiv) was combined and stirred at room temperature until LCMS confirmed disappearance of the amine starting material (approx. 18 hours). Aqueous sodium carbonate was added and then extracted with DCM. The organics were dried over sodium sulfate and concentrated to give a solid (420 mg) that was used without further purification.

Workup

  1. extractionextracted with DCM
  2. dry with materialThe organics were dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6c3f25d81db145a0bc3b9263580fb6a4
Source dataset
uspto-grants-2010_04
Patent number
US07705005B2

Reaction notes

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