Water → HCID 123476531, compound

HRID 1501879Notes

Reaction equation

HRID 1501879 reaction equation
[Br:1][C:2]1[C:3]2[CH:22]=[CH:21][CH:20]=[CH:19][C:4]=2[C:5]2[CH2:6][N:7]([C@H:12]3[CH2:17][CH2:16][CH2:15][CH2:14][C@@H:13]3[OH:18])[C:8](=[O:11])[C:9]=2[CH:10]=1.N1C(C)=CC=CC=1C.FC(F)(F)S(O[Si:37]([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:39])[CH3:38])(=O)=O.O>ClCCl>[Br:1][C:2]1[C:3]2[CH:22]=[CH:21][CH:20]=[CH:19][C:4]=2[C:5]2[CH2:6][N:7]([C@H:12]3[CH2:17][CH2:16][CH2:15][CH2:14][C@@H:13]3[O:18][Si:37]([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:39])[CH3:38])[C:8](=[O:11])[C:9]=2[CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 79372,6-LutidineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 68626060HCID 68626060, compound

Product 1

HCID 123476531HCID 123476531, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-bromo-2-[(1S,2S)-2-hydroxycyclohexyl]-1,2-dihydro-3H-benzo[e]isoindol-3-one (see Example 1, 2.00 g, 5.55 mmol) in 15 mL of dichloromethane at 0° C. was added 2,6-lutidine (1.29 mL, 11.1 mmol) and tert-butyldimethylsilyl trifluoromethanesulfonate (1.91 mL, 8.33 mmol). The mixture was warmed to ambient temperature and after 15 hr, was treated with water. The mixture was extracted 2× with ethyl acetate and the combined organic extracts were washed with brine, dried with magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified via silica gel chromatography, eluting with 0-40% ethyl acetate in hexanes, to provide 5-bromo-2-[(1S,2S)-2-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl]-1,2-dihydro-3H-benzo[e]isoindol-3-one that gave a mass ion (ES+) of 475.1 for [M+H]+.

Workup

  1. extractionThe mixture was extracted 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. customThe residue was purified via silica gel chromatography
  7. washeluting with 0-40% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-f93f0a5479b34f609c038208d7de309a
Source dataset
uspto-grants-2015_12
Patent number
US09206200B2

Reaction notes

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