Dimethyl Sulfide → HCID 67344360, compound

HRID 1669487Notes

Reaction equation

HRID 1669487 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:36]([O:38][CH3:39])=[O:37])=[CH:12][C:13]=3[N:14]3[C:21]=2[C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[O:18][CH2:17][CH:16]([CH2:26][CH2:27][C:28](=O)[N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[CH2:15]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CSC>C1COCC1>[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:36]([O:38][CH3:39])=[O:37])=[CH:12][C:13]=3[N:14]3[C:21]=2[C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[O:18][CH2:17][CH:16]([CH2:26][CH2:27][CH2:28][N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[CH2:15]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 1068Dimethyl SulfideHCID 67344803HCID 67344803, compound

Product 1

HCID 67344360HCID 67344360, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 14-cyclohexyl-7-(3-oxo-3-piperazin-1-ylpropyl)-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate (0.08 M) in THF was treated dropwise with BH3 DMS complex (2M in THF; 10 eq). The resulting solution was stirred at RT for 2.5 h. The reaction was quenched by the careful addition of HCl/MeOH (1.25 M) and the resulting solution refluxed for 2 h. The volatiles were then removed in vacuo and the residue partitioned between sat. aq. NaHCO3 and EtOAc. The combined organics were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to afford the product as a yellow foam (100%) that was used without further purification. (ES+) m/z 516 (M+H)+.

Workup

  1. customThe reaction was quenched by the careful addition of HCl/MeOH (1.25 M)
  2. temperaturethe resulting solution refluxed for 2 h
  3. customThe volatiles were then removed in vacuo
  4. customthe residue partitioned between sat. aq. NaHCO3 and EtOAc
  5. washThe combined organics were washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0535fda1b3244239bf65b3aed7655e70
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Reaction notes

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