Pyridine → HCID 10839444, compound

HRID 1058185Notes

Reaction equation

HRID 1058185 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][C:13]=1[P:22]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:23].N1C=CC=CC=1.[C:42](Cl)(=[O:44])[CH3:43].[Cl-].[NH4+]>C(Cl)Cl>[C:42]([NH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][C:13]=1[P:22]([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)=[O:23])(=[O:44])[CH3:43]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 25517Ammonium ChlorideHCID 11465546HCID 11465546, compound

Product 1

HCID 10839444HCID 10839444, compoundYield 101%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

141 mg (0.30 mmol) of (−)-2-amino-2′-diphenylphosphinyl-1,1′-binaphthyl (the formula (1-1a-1)) was dissolved in 6 ml of methylene chloride, followed by the addition of 29 μl (0.36 mmol) of pyridine and 24 μl (0.33 mmol) of acetyl chloride under 0° C. The reaction mixture was stirred at room temperature for 1 hour. To the reaction solution, 10 ml of saturated aqueous solution of ammonium chloride was added and extracted with 50 ml of methylene chloride. The extract was washed with 20 ml of brine, and then dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure. The residue was purified using a silica gel column chromatography (eluent: 1:4 mixture of ethyl acetate and hexane) to obtain 155 mg of the titled compound.

Workup

  1. extractionextracted with 50 ml of methylene chloride
  2. washThe extract was washed with 20 ml of brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under a reduced pressure
  5. customThe residue was purified
  6. additiona silica gel column chromatography (eluent: 1:4 mixture of ethyl acetate and hexane)

Sources & evidence

ORD record
ord-9f468cbe01b24735922963f2359cc4e3
Source dataset
uspto-grants-2003_02
Patent number
US06515156B2

Reaction notes

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