Acetic Acid → HCID 59264602, compound

HRID 646201Notes

Reaction equation

HRID 646201 reaction equation
[CH3:1][C:2]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)([CH3:7])[C:3]([O:5][CH3:6])=[O:4].[F:15][C:16]([F:32])([F:31])[C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][C:26]([CH2:29][NH2:30])=[CH:25][CH:24]=2)=[CH:19][CH:18]=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:8]1[CH2:13][CH2:12][CH:11]([NH:30][CH2:29][C:26]2[CH:25]=[CH:24][C:23]([C:20]3[CH:21]=[CH:22][C:17]([C:16]([F:15])([F:31])[F:32])=[CH:18][CH:19]=3)=[CH:28][CH:27]=2)[CH2:10][CH2:9]1)([CH3:7])[C:3]([O:5][CH3:6])=[O:4]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 10340Sodium CarbonateHCID 37291554-(4-TRIFLUOROMETHYLPHENYL)BENZYLAMINEHCID 5049666Sodium triacetoxyborohydrideHCID 59264606HCID 59264606, compound

Product 1

HCID 59264602HCID 59264602, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of methyl 2-methyl-2-(4-oxo-1-piperidinyl)propanoate (Int. A3) (14.28 g, 1 equiv), {[4′-(trifluoromethyl)-4-biphenylyl]methyl}amine (Int. A1) (19.6 g, 0.85 equiv), DCE (300 ml), acetic acid (3.8 ml, 0.90 equiv) and sodium triacetoxyborohydride (20.7 g, 1.25 equiv) was stirred at room temperature under nitrogen for 17.5 h. Aqueous sodium carbonate (2M solution, excess) was added and stirred for 4 h, then the mixture was extracted with a mixture of diethyl ether and THF. The organic extracts were backwashed with water and brine, dried over sodium sulfate and filtered through a pad of silica gel which was rinsed with 2.5% methanol in DCM. After evaporation in vacuo, the crude product was crystallised from ether/hexane, finally at ice bath temperature, which after drying yielded a white solid (20.9 g).

Workup

  1. stirringstirred for 4 h
  2. extractionthe mixture was extracted with a mixture of diethyl ether and THF
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered through a pad of silica gel which
  5. washwas rinsed with 2.5% methanol in DCM
  6. customAfter evaporation in vacuo
  7. customthe crude product was crystallised from ether/hexane, finally at ice bath temperature, which
  8. customafter drying

Sources & evidence

ORD record
ord-4434b58834e54435aefa603c1db686ac
Source dataset
uspto-grants-2010_04
Patent number
US07705005B2

Reaction notes

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