Ammonium formate → 2-(((1,1-Dimethylethyl)diphenylsilyl)oxy)-3-(((1,1-dimethylethyl)-diphenylsilyl)oxymethyl)-1-aminocyclobutane

HRID 5962

반응식

HRID 5962 반응식
CC([Si](C1C=CC=CC=1)(C1C=CC=CC=1)O[C:7]1([N:30]=[N+]=[N-])[CH2:10][CH:9]([CH2:11][O:12][Si:13]([C:26]([CH3:29])([CH3:28])[CH3:27])([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)C1)(C)C.[CH:45]([O-:47])=O.[NH4+]>CO.[Pd]>[CH3:27][C:26]([Si:13]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[O:12][CH:11]1[CH:9]([CH2:45][O:47][Si:13]([C:26]([CH3:29])([CH3:28])[CH3:27])([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10][CH:7]1[NH2:30])([CH3:28])[CH3:29]

참가 물질

5

반응물 2

HCID 2723923Ammonium formateHCID 86747235((1,1-Dimethylethyl)diphenylsilyloxy)-3-(((1,1-dimethylethyl)diphenyl-silyl)oxymethyl)-1-azidocyclobutane

생성물 1

HCID 197942512-(((1,1-Dimethylethyl)diphenylsilyl)oxy)-3-(((1,1-dimethylethyl)-diphenylsilyl)oxymethyl)-1-aminocyclobutane수율 184.5%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

2-(((1,1-dimethylethyl)diphenylsilyloxy)-3-(((1,1-dimethylethyl)diphenyl-silyl)oxymethyl)-1-azidocyclobutane (800 mg, 1.29 mmol), the product of Step M, was dissolved in 20 mL of methanol. To this solution was added 200 mg of 5% palladium on carbon, followed by 420 mg of ammonium formate. The flask was stoppered and the reaction mixture was stirred at ambient temperature for 23 h. The reaction mixture was filtered and the filtrate concentrated under reduced pressure. The residue was dissolved in 200 mL of diethyl ether and the ether solution was washed with 100 mL of 5% aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 707 mg (92% yield) of the title compound; MS DCI-NH3M/Z: 594 (M+H)+ ; 1H NMR (CDCl3) δ 0.88-1.08 (m, 18H), 1.95-2.15 (m, 3H), 3.01 (q, 1H), 3.5 (m, 2H), 3.68 (t, 1H).

후처리

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in 200 mL of diethyl ether
  4. washthe ether solution was washed with 100 mL of 5% aqueous sodium bicarbonate solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-d7295c19f6b346c7b7c965bccf92eca4
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05246931

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