Trityl chloride → HCID 58455161, compound

HRID 80307Notes

Reaction equation

HRID 80307 reaction equation
[NH:1]1[CH2:5][CH2:4][C@@H:3]([OH:6])[CH2:2]1.[C:7]1([C:13]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)Cl)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(=O)([O-])O.[Na+]>C(#N)C>[C:7]1([C:13]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:1]2[CH2:5][CH2:4][C@@H:3]([OH:6])[CH2:2]2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 516892Sodium BicarbonateHCID 2759337(R)-3-Pyrrolidinol

Product 1

HCID 58455161HCID 58455161, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(R)-(+)-3-Pyrrolidinol (1.0 g, 11.5 mmol) (Aldrich) and triphenylchloromethane (1.00 g, 3.59 mmol) (Wako Pure Chemical Industries, Ltd.) were dissolved in acetonitrile (30 mL) (Wako Pure Chemical Industries, Ltd.), and the mixture was refluxed for 3 hours. The mixture was allowed to cool to room temperature, and then a saturated aqueous solution of sodium hydrogen carbonate (Wako Pure Chemical Industries, Ltd.) was added to the reaction solution, followed by extraction with ethyl acetate (Wako Pure Chemical Industries, Ltd.). The organic layer was dried with anhydrous sodium sulfate (Wako Pure Chemical Industries, Ltd.), and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography (chloroform (Wako Pure Chemical Industries, Ltd.) as an eluent), to thereby obtain the title compound (0.73 g, 62% yield).

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. extractionfollowed by extraction with ethyl acetate (Wako Pure Chemical Industries, Ltd.)
  3. dry with materialThe organic layer was dried with anhydrous sodium sulfate (Wako Pure Chemical Industries, Ltd.)
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-17b6ac906b664eaa906937820473dd72
Source dataset
uspto-grants-2014_09
Patent number
US08846012B2

Reaction notes

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