Pyridine → HCID 12010727, compound

HRID 1058182Notes

Reaction equation

HRID 1058182 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-abcfd45c07304ea2a5acd9e0572e921b
Source dataset
uspto-grants-2003_02
Patent number
US06515156B2

Reaction notes

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