Huagongshe화공사 화학 정보 인쇄 보고서 · 연구 참고용
Acetic Acid → 1,1-Dimethylethyl 3-[[[4-(methoxycarbonyl)phenyl]methyl]amino]-8-azabicyclo[3.2.1]octane-8-carboxylate
참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|---|---|---|
| 반응물 | Acetic Acid | HCID 176 | — |
| 반응물 | Sodium Bicarbonate | HCID 516892 | — |
| 반응물 | Methyl 4-(aminomethyl)benzoate | HCID 571728 | — |
| 반응물 | tert-butyl (1R,5S)-3-oxo-8-azabicyclo[3.2.1]octane-8-carboxylate | HCID 688612 | — |
| 반응물 | Sodium triacetoxyborohydride | HCID 5049666 | — |
| 용매 | 1,1-Dichloroethane | HCID 6365 | — |
| 생성물 | 1,1-Dimethylethyl 3-[[[4-(methoxycarbonyl)phenyl]methyl]amino]-8-azabicyclo[3.2.1]octane-8-carboxylate | HCID 68490120 | 88.2% |
반응 단계
A solution of N-Boc nortropinone (2.4 g, 10.9 mmol) and methyl 4-aminomethylbenzoate (1.6 g, 10.9 mmol) in dichloroethane (20 mL) was stirred as acetic acid (0.85 g, 14.2 mmol) was added. After 1 hour, sodium triacetoxyborohydride (2.7 g, 13.1 mmol) was added and the reaction was stirred for 17 hours. The reaction was treated with a saturated aqueous solution of sodium bicarbonate and extracted with ethyl acetate (2×). The combined organic extracts were dried and concentrated. Purification by flash chromatography on silica gel using a gradient of ethyl acetate in hexane gave 3.6 g of 1,1-dimethylethyl 3-[[[4-(methoxycarbonyl)phenyl]methyl]amino]-8-azabicyclo[3.2.1]octane-8-carboxylate.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 특허 번호 | US07737145B2 |
| 출처 데이터셋 | uspto-grants-2010_06 |
| ORD ID | ord-a78a28ccfb4340a9954795ea6c536f8c |
| 출처 메모 | uspto-grants-2010_06 |