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Trimethyl borate → (1R)-1-(3-methanesulfonylphenyl)ethan-1-ol
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Trimethyl borate | HCID 8470 | — |
| 反応物 | 2-Pyrrolidinemethanol, alpha,alpha-diphenyl-, (R)- | HCID 7045371 | — |
| 反応物 | 1-(3-Methanesulfonylphenyl)ethan-1-one | HCID 59741437 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 生成物 | (1R)-1-(3-methanesulfonylphenyl)ethan-1-ol | HCID 66622848 | 81.7% |
反応手順
B(OMe)3 (62 μL, 0.55 mmol) was added to (R)-(+)-α,α-diphenyl-2-pyrrolidinemethanol in THF (5 mL) followed by BH3.Me3S (2M in THF, 1.23 mL, 2.54 mmol). The mixture was stirred for 1 h before 1-[3-(methylsulfonyl)phenyl]ethanone (458 mg, 2.31 mmol) in THF (5 mL) was added over 1.5 h. The resulting mixture was stirred overnight and then quenched with 1M HCl (2 mL). The mixture was concentrated and the crude product was purified by flash column chromatography (CH2Cl2/MeOH 50:1) to give the title compound (378 mg, 18% yield).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08088780B2 |
| 出典データセット | uspto-grants-2012_01 |
| ORD ID | ord-e3fafe93775640ec8fbc1ed11a1b790a |
| 出典メモ | uspto-grants-2012_01 |