Reaktion #2278392

Reaktionsgleichung

toluene

(Z)-benzyl 7,9-dimethyl-5-(2-methyl-2H-tetrazol-5-ylimino)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carboxylate

(E)-benzyl 7,9-dimethyl-5-(2-methyl-2H-tetrazol-5-ylamino)-2,3-dihydro-1H-benzo[b]azepine-1-carboxylate

→

title compound

(S)-benzyl 7,9-dimethyl-5-(2-methyl-2H-tetrazol-5-ylamino)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carboxylate

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONCharge an autoclave
2. 2
   SonstigePurge the autoclave with nitrogen
3. 3
   TemperaturWhile maintaining an oxygen free environment
4. 4
   workup.ADDITIONadd
5. 5
   Sonstigeseal the autoclave
6. 6
   TemperaturCool the reaction mixture to RT
7. 7
   FiltrationFilter the solids
8. 8
   Sonstigecollect the organic mixture
9. 9
   WaschenWash the organic mixture with water (2×25 mL)
10. 10
    Trocknendry over Na2SO4
11. 11
    Filtrationfilter
12. 12
    SonstigeCollect the filtrate
13. 13
    Sonstigeremove the solvent under vacuum

Vorschrift

Charge an autoclave with a mixture of (Z)-benzyl 7,9-dimethyl-5-(2-methyl-2H-tetrazol-5-ylimino)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carboxylate and (E)-benzyl 7,9-dimethyl-5-(2-methyl-2H-tetrazol-5-ylamino)-2,3-dihydro-1H-benzo[b]azepine-1-carboxylate (4.04 g, 10 mmole), S-(−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl ((S)-BINAP, 60 mg, 96.3 μmoles), KI (415 mg 24 mmoles, KI can be deleted if desired) and di chloro-bis((1,2,5,6 eta)-1,5-cyclooctadiene)diiridium (Ir2Cl2(COD)2 (927 mg 40.2 μmoles). Purge the autoclave with nitrogen. While maintaining an oxygen free environment, add degassed toluene (50 mL, 472.8 mmol) and seal the autoclave. Heat to 100° C. under 500 psi H2 for 66 h. Cool the reaction mixture to RT and vent. Filter the solids and collect the organic mixture. Wash the organic mixture with water (2×25 mL); dry over Na2SO4, and filter. Collect the filtrate and remove the solvent under vacuum to provide the title compound (3.99 g, 88.7% ee by HPLC).

Quelle