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3-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde, (R)-(+)- → tert-Butyl (4S)-4-ethynyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | 3-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde, (R)-(+)- | HCID 178792 | — |
| 反応物 | Diazomethyl-phosphonic-acid-diethylester | HCID 10943016 | — |
| 反応物 | Potassium tert-butoxide | HCID 23665647 | — |
| 溶媒 | Diethyl Ether | HCID 3283 | — |
| 生成物 | tert-Butyl (4S)-4-ethynyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate | HCID 11160457 | — |
反応手順
(S)-N-Boc-2,2-dimethyl-4-ethynyl-oxazolidine was prepared according to Method X above by the treatment of tert-butyl-(R)-4-formyl-2,2-dimethyl-3-oxazolidine-carboxylate (1.00 g, 4.36 mmol) (Aldrich) with potassium tert-butoxide (730 mg, 6.54 mmol) and diazomethyl-phosphonic-acid-diethylester (1.20 g, 6.54 mmol) (Method X above). The reaction was allowed slowly to warm up to room temperature and stirred for a total of 12 hrs. (S)-N-Boc-2,2-dimethyl-4-ethynyl-oxazolidine was obtained after silica gel column chromatography with 20% Et2O in hexanes. (Yield 420 mg, 43%).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US06130239 |
| 出典データセット | uspto-grants-2000_10 |
| ORD ID | ord-ad3086333bef492fb2b5ef584b0234ea |
| 出典メモ | uspto-grants-2000_10 |