Pyridine → HCID 12010727, compound

HRID 430867Notes

Reaction equation

HRID 430867 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:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.N1C=CC=CC=1.Cl[C:42]([O:44][CH3:45])=[O:43].[Cl-].[NH4+]>C(Cl)Cl>[CH3:45][O:44][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:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[O:43]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6586Methyl chloroformateHCID 25517Ammonium ChlorideHCID 10694978HCID 10694978, compound

Product 1

HCID 12010727HCID 12010727, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.20 gram (2.65 mmol) of (−)-2-amino-2′-diphenylphosphino-1,1′-binaphthyl (1-1a) was dissolved in 53 ml of methylene chloride, followed by the addition of 0.26 ml (3.18 mmol) of pyridine and 0.23 ml (2.91 mmol) of methyl chloroformate under 0° C. The reaction mixture was stirred at room temperature for 21 hours. To the reaction solution, 40 ml of saturated aqueous solution of ammonium chloride was added and extracted with 100 ml of methylene chloride. The extract was washed with 80 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 1.25 gram of the titled compound.

Workup

  1. extractionextracted with 100 ml of methylene chloride
  2. washThe extract was washed with 80 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-66a4d9718f3d4acabdfe88f6a6737fdf
Source dataset
uspto-grants-2001_11
Patent number
US06323353B1

Reaction notes

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