반응 #1434

반응 방정식

triphenylchloromethane

Hydrazine monohydrate

(S)-hexahydro-6-phthalimido-2,2-dimethyl-2H-azepine-7-one

triphenylchloromethane

triethylamine

→

title product

(S)-Hexahydro-6-[(triphenylmethyl)amino]-2,2-dimethyl-2H-azepine-7-one

용매

methanol

반응 조건

후처리

1. 1
   여과then filtered
2. 2
   기타to remove the white precipitate
3. 3
   기타The volatiles were evaporated
4. 4
   workup.DISSOLUTIONthe residue was dissolved in methylene chloride (560 ml.)
5. 5
   여과filtered
6. 6
   기타to remove additional precipitate
7. 7
   workup.STIRRINGthe resulting mixture was stirred for 1.5 hours
8. 8
   기타the solvent was removed
9. 9
   기타The residue was partitioned between ethyl acetate and water
10. 10
    세척The organic layer was washed with brine
11. 11
    기타dried
12. 12
    여과filtered
13. 13
    농축concentrated
14. 14
    기타to give a pale yellow foam
15. 15
    기타a crystallization from ethyl acetate and hexanes, 7.47 g

실험 절차

Hydrazine monohydrate (4.59 ml., 94.6 mmol.) was added to a solution of (S)-hexahydro-6-phthalimido-2,2-dimethyl-2H-azepine-7-one [prepared as described in Example 66(e), 19.98 g., 68.76 mmol.] in methanol (250 ml.) at room temperature under argon. The resulting mixture was stirred for 72 hours then filtered to remove the white precipitate. The volatiles were evaporated and the residue was dissolved in methylene chloride (560 ml.) and filtered to remove additional precipitate. To this filtrate was added triethylamine (13.3 ml., 96.21 mmol.) followed by triphenylchloromethane (20.65 g., 74.07 mmol.) and the resulting mixture was stirred for 1.5 hours. Additional triphenylchloromethane (958 mg., 3.44 mmol.) was added and the solvent was removed. The residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried, filtered and concentrated to give a pale yellow foam. Following a crystallization from ethyl acetate and hexanes, 7.47 g. of title product was obtained as off-white crystals. The mother liquor was concentrated and crystallized from ethyl acetate and pentane to give a second crop (8.02 g.) of title product. The mother liquor was concentrated and the residue was flash chromatographed (E Merck silica gel) eluting with 4.5:5.5 ethyl acetate/hexanes to give 6.0 g of title compound as a white foam. The combined yield of title product was 21.49 g.; m.p. 139°-140° C.; [α]D =+43.4° (c=0.37, methylene chloride). TLC (2:3 hexane: ethyl acetate) Rf =0.63.

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