Tetrahydrofuran → methyl (7R)-7-azido-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

HRID 1714015Notes

Reaction equation

HRID 1714015 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:37]([O:39][CH3:40])=[O:38])=[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][C@@H:16](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:15]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1COCC1.[N:46]([Si](C)(C)C)=[N+:47]=[N-:48]>>[N:46]([C@@H:16]1[CH2:15][N:14]2[C:13]3[CH:12]=[C:11]([C:37]([O:39][CH3:40])=[O:38])[CH:10]=[CH:9][C:8]=3[C:7]([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)=[C:21]2[C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[O:18][CH2:17]1)=[N+:47]=[N-:48]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 78378AzidotrimethylsilaneHCID 50994749methyl (7S)-14-cyclohexyl-7-{[(4-methylphenyl)sulfonyl]oxy}7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

Product 1

HCID 50994750methyl (7R)-7-azido-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylateYield 84%

Conditions

Temperature
65 °C

Procedure

To a solution of the foregoing product from step 1 in dry THF (0.06 M) azidotrimethylsilane (3.5 eq.) and tetrabutylammonium triphenyldifluorosilicate (3.5 eq.) were added. The reaction was stirred for 20 h at 65° C. then 1 more eq. of azidotrimethylsilane was added and the mixture stirred at 65° C. for 36 h. The volatiles were evaporated in vacuo and the crude dissolved in EtOAc was washed with hydrochloric acid (1 N), sodium hydrogen carbonate (saturated solutions) and brine. Drying over Na2SO4, filtration and concentration in vacuo gave the crude product, which was purified by flash chromatography on silica gel (5:95 EtOAc/PE) to afford the title compound as white foam (84%); MS (ES+) m/z 431 (M+H)+.

Workup

  1. stirringthe mixture stirred at 65° C. for 36 h
  2. customThe volatiles were evaporated in vacuo
  3. dissolutionthe crude dissolved in EtOAc
  4. washwas washed with hydrochloric acid (1 N), sodium hydrogen carbonate (saturated solutions) and brine
  5. dry with materialDrying over Na2SO4, filtration and concentration in vacuo
  6. customgave the crude product, which
  7. customwas purified by flash chromatography on silica gel (5:95 EtOAc/PE)

Sources & evidence

ORD record
ord-9657229fe6cd401d93223ce02b47a746
Source dataset
uspto-grants-2010_09
Patent number
US07795247B2

Reaction notes

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