Potassium Hydroxide → HCID 86669679, compound

HRID 1623938Notes

Reaction equation

HRID 1623938 reaction equation
[OH-].[K+].[CH2:3]1[CH:5]2[CH2:6][C:7]3[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N:9][NH:10][C:11]=3[CH:4]12.Br[CH2:18][CH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O>CS(C)=O>[O:22]1[CH2:23][CH2:24][CH:19]([CH2:18][N:10]2[C:11]3[C@@H:4]4[CH2:3][C@@H:5]4[CH2:6][C:7]=3[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N:9]2)[CH2:20][CH2:21]1

Participants

6

Reactant 4

HCID 14797Potassium HydroxideHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 27732864-(Bromomethyl)oxaneHCID 69059432HCID 69059432, compound

Product 1

HCID 86669679HCID 86669679, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To potassium hydroxide (561 mg, 10.00 mmol) in DMSO (10 mL) was added ethyl 1a,2,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carboxylate (356 mg, 1.852 mmol) under nitrogen atmosphere. The mixture was stirred at room temperature for 1 hour and added 4-(bromomethyl)tetrahydro-2H-pyran (962 mg, 5.37 mmol). The reaction was stirred at room temperature for 1.5 h, poured into 50 mL of ice cold water and added glacial acetic (0.71 mL). The resulting mixture was extracted with EtOAc (3×50 mL). The combined organic extracts were concentrated under reduced pressure and purified by HPLC to give the title compound (127 mg, 24% yield) as a yellow solid. LCMS m/z=291.2 [M+H]+.

Workup

  1. stirringThe reaction was stirred at room temperature for 1.5 h
  2. extractionThe resulting mixture was extracted with EtOAc (3×50 mL)
  3. concentrationThe combined organic extracts were concentrated under reduced pressure
  4. custompurified by HPLC

Sources & evidence

ORD record
ord-dc237dc3cadd4db092a53b3db60bdc25
Source dataset
uspto-grants-2014_07
Patent number
US08778950B2

Reaction notes

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