Potassium Carbonate → HCID 86635702, compound

HRID 598907Notes

Reaction equation

HRID 598907 reaction equation
[C:1]([O-])([O-])=O.[K+].[K+].O[C@@H:8]1[CH2:12][CH2:11][C@H:10]([CH2:13][C:14]2[CH:15]=[N:16][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:19]=2)[N:9]1[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25].O[C@H]1CC[C@H](CC2C=NC(C(F)(F)F)=CC=2)N1C(OC(C)(C)C)=O>CO.O>[F:22][C:20]([F:23])([F:21])[C:17]1[N:16]=[CH:15][C:14]([CH2:13][C@H:10]([NH:9][C:24](=[O:25])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:11][CH2:12][C:8]#[CH:1])=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 67062678HCID 67062678, compoundHCID 67062709HCID 67062709, compound

Product 1

HCID 86635702HCID 86635702, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Dimethyl 1-diazo-2-oxopropyl phosphonate (505 mg, 2627 μmol) (commercially available from TCI America Organic Chemicals Product List (Order Number D3546)), followed by K2CO3 (545 mg, 3941 μmol) was added to a diastereomeric mixture of (2R,5R)-tert-butyl 2-hydroxy-5-((6-(trifluoromethyl)pyridin-3-yl)methyl)pyrrolidine-1-carboxylate and (2S,5R)-tert-butyl 2-hydroxy-5-((6-(trifluoromethyl)pyridin-3-yl)methyl)pyrrolidine-1-carboxylate (455 mg, 1314 μmol) in MeOH (1.3 mL) at room temperature. The mixture was stirred at room temperature for 4 hours, diluted with H2O (15 mL), and extracted with DCM (3×20 mL). The combined organic layers were dried (MgSO4) and concentrated under reduced pressure. The resulting yellow solid was dissolved in MeOH/DCM, absorbed onto silica gel, and purified by flash chromatography (silica gel, 10% to 30% EtOAc/hexanes) to deliver (R)-tert-butyl 1-(6-(trifluoromethyl)pyridin-3-yl)hex-5-yn-2-ylcarbamate (284 mg, 63%) as an off-white solid. LCMS (API-ES) m/z: 343.1 (M+H+).

Workup

  1. extractionextracted with DCM (3×20 mL)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe resulting yellow solid was dissolved in MeOH/DCM
  5. customabsorbed onto silica gel
  6. custompurified by flash chromatography (silica gel, 10% to 30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-c6e0e922adeb46ba9cee8c35f41a2e31
Source dataset
uspto-grants-2011_03
Patent number
US07897619B2

Reaction notes

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