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Triphenylphosphine → (R)-di-tert-butyl 1-((tetrahydrofuran-2-yl)methyl)hydrazine-1,2-dicarboxylate
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Triphenylphosphine | HCID 11776 | — |
| 反応物 | Di-tert-butyl bicarbamate | HCID 85431 | — |
| 反応物 | Di-tert-butyl diazene-1,2-dicarboxylate | HCID 6034084 | — |
| 反応物 | (2R)-oxolan-2-ylmethanol | HCID 6931745 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 生成物 | (R)-di-tert-butyl 1-((tetrahydrofuran-2-yl)methyl)hydrazine-1,2-dicarboxylate | HCID 66643239 | 95.2% |
反応手順
To a mixture of (R)-(tetrahydrofuran-2-yl)methanol (Fluka, 4.0 g, 39.2 mmol) and di-tert-butyl hydrazine-1,2-dicarboxylate (9.1 g, 39.2 mmol) in THF (50 mL) was added triphenylphosphine (14.4 g, 54.8 mmol) followed by (E)-di-tert-butyl diazene-1,2-dicarboxylate (12.6 g, 54.8 mmol) portionwise. This mixture was stirred at ambient temperature for 16 hours then concentrated under reduced pressure and purified by column chromatography (SiO2, 1-25% EtOAc/hexanes gradient) to give the title compound (11.8 g, 37.3 mmol, 95% yield). MS (DCI/NH3) m/z 317 (M+H)+.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08188135B2 |
| 出典データセット | uspto-grants-2012_05 |
| ORD ID | ord-416fcca2343540c29303ce8b5697909e |
| 出典メモ | uspto-grants-2012_05 |