Benzhydrylamine → HCID 66925132, compound

HRID 554383Notes

Reaction equation

HRID 554383 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:14][C:13]([CH:22]=O)=[CH:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:24]1([CH:30]([NH2:37])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:14][C:13]([CH2:22][NH:37][CH:30]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7036BenzhydrylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86232905HCID 86232905, compound

Product 1

HCID 66925132HCID 66925132, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension (12 mL) of 1-[(4-methylphenyl)sulfonyl]-5-phenyl-1H-pyrrole-3-carbaldehyde (1.2 g), diphenylmethylamine (1.35 g) and powder molecular sieves 4A (5.0 g) in dichloromethane was stirred at room temperature for 6 hr, sodium triacetoxyborohydride (1.56 g) was added, and the mixture was further stirred at room temperature for 3 hr. The reaction mixture was filtered through celite, and the filtrate was partitioned using an ethyl acetate-saturated aqueous sodium hydrogencarbonate solution. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→1:1). The obtained oil was left standing in a freezer (temperature: −20° C.) to give the title compound as a colorless solid (yield 1.61 g, 89%).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customthe filtrate was partitioned
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→1:1)
  7. waitThe obtained oil was left
  8. customstanding in a freezer (temperature: −20° C.)

Sources & evidence

ORD record
ord-a967d44a11394a08842dc77b10d68c73
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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