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Methanol → tert-butyl (1R*,4S*,6R*)-4-(hydroxymethyl)-3-azabicyclo[4.1.0]heptane-3-carboxylate
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Methanol | HCID 887 | — |
| 反応物 | Tetrahydrofuran | HCID 8028 | — |
| 反応物 | Lithium hydroxide, monohydrate | HCID 168937 | — |
| 反応物 | tert-butyl (1R*,4S*,6R*)-4-({[(4-nitrophenyl)carbonyl]oxy}methyl)-3-azabicyclo[4.1.0]heptane-3-carboxylate | HCID 86676232 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | Sodium chloride; water | HCID 57417360 | — |
| 生成物 | tert-butyl (1R*,4S*,6R*)-4-(hydroxymethyl)-3-azabicyclo[4.1.0]heptane-3-carboxylate | HCID 49844664 | 70.7% |
反応手順
To a mixture of tert-butyl (1R*,4S*,6R*)-4-({[(4-nitrophenyl)carbonyl]oxy}methyl)-3-azabicyclo[4.1.0]heptane-3-carboxylate (8.2 g) produced above, tetrahydrofuran (70 mL), methanol (70 mL) and water (35 mL) was added lithium hydroxide monohydrate (2.7 g). The mixture was stirred at room temperature for 1 hr. The reaction mixture was diluted with brine, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate. Insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (3.5 g).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08722660B2 |
| 出典データセット | uspto-grants-2014_05 |
| ORD ID | ord-e2100ea2ab414ca6bc6da55aa3085012 |
| 出典メモ | uspto-grants-2014_05 |