Dichloromethane → HCID 86682407, compound

HRID 2365259Notes

Reaction equation

HRID 2365259 reaction equation
ClCCl.[Br:4][C:5]1[C:6]2[C:11]([C:12]3[CH2:17][N:16]([C@H:18]4[CH2:23][CH2:22][CH2:21][CH2:20][C@@H:19]4[OH:24])[C:15](=[O:25])[C:13]=3[CH:14]=1)=[N:10][CH2:9][CH2:8][CH:7]=2.N1C(C)=CC=CC=1C.FC(F)(F)S(O[Si:40]([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:42])[CH3:41])(=O)=O>O>[Br:4][C:5]1[CH:14]=[C:13]2[C:15](=[O:25])[N:16]([C@H:18]3[CH2:23][CH2:22][CH2:21][CH2:20][C@@H:19]3[O:24][Si:40]([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:42])[CH3:41])[CH2:17][C:12]2=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[N:10]2

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 79372,6-LutidineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 86682408HCID 86682408, compound

Product 1

HCID 86682407HCID 86682407, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 15 mL dichloromethane solution of 5-bromo-8-[(1S,2S)-2-hydroxycyclohexyl]-3,9-dihydro-7H-pyrrolo[3,4-h]quinolin-7-one (2.00 g, 5.54 mmol) at 0° C. was added 2,6 lutidine (1.29 mL, 11.1 mmol) and tert-butyldimethylsilyl trifluoromethanesulfonate (1.91 mL, 8.30 mmol). The mixture was warmed to ambient temperature, and after 15 hr, diluted with water and extracted 2× with ethyl acetate. The combined organic extracts were washed with brine, dried with magnesium sulfate, filtered, and concentrated in vacuo. The resultant white crystals were collected via filtration and washed with hexanes to provide 5-bromo-8-[(1S,2S)-2-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl]-8,9-dihydro-7H-pyrrolo[3,4-h]quinolin-7-one that gave a proton NMR spectra consistent with theory.

Workup

  1. extractionextracted 2× with ethyl acetate
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. filtrationThe resultant white crystals were collected via filtration
  7. washwashed with hexanes

Sources & evidence

ORD record
ord-8581bc7696304c439ca486e50051c55f
Source dataset
uspto-grants-2014_04
Patent number
US08697690B2

Reaction notes

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