Pyridine → HCID 12010732, compound

HRID 1058188Notes

Reaction equation

HRID 1058188 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.[CH3:42][S:43](Cl)(=[O:45])=[O:44].[Cl-].[NH4+]>C(Cl)Cl>[CH3:42][S:43]([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:45])=[O:44]

Participants

6

Reactant 4

HCID 1049PyridineHCID 25517Ammonium ChlorideHCID 31297Methanesulfonyl chlorideHCID 11465546HCID 11465546, compound

Product 1

HCID 12010732HCID 12010732, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6.62 gram (14.1 mmol) of (−)-2-amino-2′-diphenylphosphinyl-1,1′-binaphthyl (the formula (1-1a-1)) was dissolved in 282 ml of methylene chloride, followed by the addition of 4.7 ml (57.8 mmol) of pyridine and 4.1 ml (53.6 mmol) of methanesulfonyl chloride at 0° C. The reaction solution was stirred at room temperature for 23 hours. To the reaction solution, 200 ml of saturated aqueous solution of ammonium chloride was added and extracted with 200 ml of methylene chloride. The extract was washed with 200 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: 2:3 mixture of ethyl acetate and hexane) to obtain 6.15 gram of the titled compound.

Workup

  1. extractionextracted with 200 ml of methylene chloride
  2. washThe extract was washed with 200 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: 2:3 mixture of ethyl acetate and hexane)

Sources & evidence

ORD record
ord-180a5517593b421cba34782e12fde342
Source dataset
uspto-grants-2003_02
Patent number
US06515156B2

Reaction notes

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