반응 #160046

반응 방정식

tert-butyl 10-benzyl-8-phenyl-7-oxa-3,10-diazaspiro[5.5]undecane-3-carboxylate

ammonium formate

→

tert-butyl 8-phenyl-7-oxa-3,10-diazaspiro[5.5]undecane-3-carboxylate

수율 93.0%

용매

ethanol

반응 조건

후처리

1. 1
   온도The reaction mixture was cooled
2. 2
   여과filtered
3. 3
   농축concentrated to 10% of original volume
4. 4
   workup.ADDITIONdiluted with ethyl acetate
5. 5
   세척washed with sat. aq. NaHCO3 (pH 10)/brine
6. 6
   추출The aqueous was extracted further with ethyl acetate
7. 7
   건조the combined organics were dried over Na2SO4
8. 8
   여과filtered
9. 9
   농축concentrated in vacuo

실험 절차

To tert-butyl 10-benzyl-8-phenyl-7-oxa-3,10-diazaspiro[5.5]undecane-3-carboxylate (1.58 g, 3.74 mmol) and Pd(OH)2 (280 mg, 0.40 mmol) in ethanol (16 mL) was added ammonium formate (1.10 g, 17.39 mmol) and the reaction mixture was heated to 60° C. for 40 min. The reaction mixture was cooled, filtered, concentrated to 10% of original volume, diluted with ethyl acetate and washed with sat. aq. NaHCO3 (pH 10)/brine. The aqueous was extracted further with ethyl acetate and the combined organics were dried over Na2SO4, filtered and concentrated in vacuo to give tert-butyl 8-phenyl-7-oxa-3,10-diazaspiro[5.5]undecane-3-carboxylate (1.15 g, 93%) as a white solid. ESI-MS m/z calc. 332.2. Found 333.3 (M+1)+; Retention time: 1.13 minutes (3 min run). 1H NMR (400 MHz, CDCl3) δ 7.40-7.23 (m, 5H), 4.69 (dd, J=10.7, 2.7 Hz, 1H), 3.76 (br. s, 2H), 3.31 (t, J=10.7 Hz, 1H), 3.17-3.02 (m, 2H), 2.75 (dd, J=35.5, 12.4 Hz, 2H), 2.63 (dd, J=12.3, 10.8 Hz, 1H), 2.49 (d, J=12.5 Hz, 1H), 1.69-1.57 (m, J=12.6 Hz, 1H), 1.57-1.39 (m, 11H).

출처