Sodium hydride → HCID 59660701, compound

HRID 1641433Notes

Reaction equation

HRID 1641433 reaction equation
[H-].[Na+].[N:3]1([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4]1.[C:15]([O:19][C:20]([N:22]1[CH2:26][CH2:25][CH2:24][C@@H:23]1[CH2:27]OS(C1C=CC(C)=CC=1)(=O)=O)=[O:21])([CH3:18])([CH3:17])[CH3:16]>CN(C=O)C>[C:15]([O:19][C:20]([N:22]1[CH2:26][CH2:25][CH2:24][C@@H:23]1[CH2:27][O:14][C:11]1[CH:12]=[CH:13][C:8]([N:3]2[CH:4]=[CH:5][CH:6]=[CH:7]2)=[CH:9][CH:10]=1)=[O:21])([CH3:18])([CH3:16])[CH3:17]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 90072p-(1H-Pyrrol-1-yl)phenolHCID 11760051(R)-tert-Butyl 2-((tosyloxy)methyl)pyrrolidine-1-carboxylate

Product 1

HCID 59660701HCID 59660701, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 25 mL vial which contained a suspension of NaH (60% in mineral oil, 60 mg, 1.5 mmol) in DMF (5 mL) was added 4-Pyrrol-1-yl-phenol (160 mg, 1 mmol) at 0° C. The mixture was allowed to warm to rt and stir at rt for 30 min then cooled to 0° C. To this reaction mixture was added (R)-2-(toluene-4-sulfonyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (355 mg, 1 mmol) at 0° C. The resulting mixture was allowed to warm to rt and stir at rt for 30 min and then was heated to 90° C. and stirred at 90° C. for 16 h. After cooled to rt, the mixture was poured into 150 mL ice-water solution and then was extracted with EtOAc (3×50 mL). The combined organic layers were washed with water (3×50 mL) and brine (30 mL), dried over Na2SO4. After concentrated in vacuo, the residue was purified by a column chromatography on silica gel eluting with ethyl ethyl acetate:hexane (1:10-1:4) to yield the title compound (270 mg, 80%); LCMS; m/z (ESI+ 243.3, M+1); 99%;

Workup

  1. temperaturethen cooled to 0° C
  2. temperatureto warm to rt
  3. stirringstir at rt for 30 min
  4. temperaturewas heated to 90° C.
  5. stirringstirred at 90° C. for 16 h
  6. temperatureAfter cooled to rt
  7. extractionwas extracted with EtOAc (3×50 mL)
  8. washThe combined organic layers were washed with water (3×50 mL) and brine (30 mL)
  9. dry with materialdried over Na2SO4
  10. concentrationAfter concentrated in vacuo
  11. customthe residue was purified by a column chromatography on silica gel eluting with ethyl ethyl acetate:hexane (1:10-1:4)

Sources & evidence

ORD record
ord-e252c29365bb4011a701635612c0fab3
Source dataset
uspto-grants-2012_02
Patent number
US08115005B2

Reaction notes

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