참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Hexamethylphosphoramide | HCID 12679 | — |
| 반응물 | Carbonocyanidic acid, methyl ester | HCID 28660 | — |
| 반응물 | Lithium diisopropylamide | HCID 2724682 | — |
| 반응물 | 4-(2-Benzyloxyethyl)cyclohexanone | HCID 21879605 | — |
| 용매 | Tetrahydrofuran | HCID 8028 | — |
| 생성물 | 5-(2-Benzyloxy-ethyl)-2-oxo-cyclohexanecarboxylic acid methyl ester | HCID 57443243 | — |
반응 단계
A solution of LDA (33 ml, 1.5 M in Et2O) in THF (50 mL) at −78° C. was treated with 4-(2-benzyloxy-ethyl)-cyclohexanone (9.5 g, 40.2 mmol). The mixture was warmed to 0° C. over 30 m before re-cooling to −78° C. and adding HMPA (7 mL). Methyl cyanoformate (4.1 mL, 85 mmol) was added and the mixture was stirred for 15 m before aqueous quench and work-up. The product was purified by chromatography on SiO2 with 10% EtOAc:Hx. 5-(2-Benzyloxy-ethyl)-2-oxo-cyclohexanecarboxylic acid methyl ester was isolated, 5.8 g (49%) and reduced with an equivalent of NaBH4 in MeOH at −10° C. to provide the alcohol (Intermediate R2). Intermediate R2 was purified by chromatography on SiO2 with 30 to 50% EtOAC:Hx. (˜90% yield).
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 특허 번호 | US07419994B2 |
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| 출처 데이터셋 | uspto-grants-2008_09 |
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| ORD ID | ord-b7058c7b568a446c9a7a2baaab627763 |
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| 출처 메모 | uspto-grants-2008_09 |
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