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tert-Butyldimethylsilyl chloride → 1-Benzyl-3-(R)-(t-butyldimethylsilyloxymethyl)-4-(S)-phenylpyrrolidine
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | tert-Butyldimethylsilyl chloride | HCID 28928 | — |
| 反応物 | Diisopropylethylamine | HCID 81531 | — |
| 反応物 | ((3R,4S)-1-Benzyl-4-phenylpyrrolidin-3-YL)methanol | HCID 21341047 | — |
| 溶媒 | Dichloromethane | HCID 6344 | — |
| 生成物 | 1-Benzyl-3-(R)-(t-butyldimethylsilyloxymethyl)-4-(S)-phenylpyrrolidine | HCID 21341048 | 100% |
反応手順
A solution of 82.0 g (0.31 mol) of 1-benzyl-3-(R)-hydroxymethyl-4-(S)-phenyl pyrrolidine (from EXAMPLE 1, Step C) and 46.5 g (0.36 mol) of DIEA in 1 L of CH2Cl2 was treated with 54.2 g (0.36 mol) of t-butyldimethylsilyl chloride and the resulting mixture was stirred at rt for 20 h. The reaction was quenched with 750 mL of sat'd NaHCO3 and the layers were separated. The organic layer was combined with 150 g of silica gel and aged for 45 min. The mixture was filtered and the filtrate was concentrated to afford 117 g (100%) of the title compound.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US06265434B1 |
| 出典データセット | uspto-grants-2001_07 |
| ORD ID | ord-75bda224aaaa4b239fd91881f5a75b34 |
| 出典メモ | uspto-grants-2001_07 |