Pyridine → (S)-tert-butyl 3-(acetamidomethyl)morpholine-4-carboxylate

HRID 1771208

反応式

HRID 1771208 の反応式
[NH2:1][CH2:2][C@H:3]1[CH2:8][O:7][CH2:6][CH2:5][N:4]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].N1C=CC=CC=1.[C:22](Cl)(=[O:24])[CH3:23]>ClCCl.C(=O)(O)[O-].[Na+].[Cl-].[Na+]>[C:22]([NH:1][CH2:2][C@H:3]1[CH2:8][O:7][CH2:6][CH2:5][N:4]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])(=[O:24])[CH3:23]

参加物

7

反応物 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 44182324(S)-tert-Butyl 3-(aminomethyl)morpholine-4-carboxylate

生成物 1

HCID 66723613(S)-tert-butyl 3-(acetamidomethyl)morpholine-4-carboxylate

試薬・触媒・溶媒 3

HCID 5234Sodium Chloride溶媒HCID 6344Dichloromethane溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

To a solution of (S)-tert-butyl 3-(aminomethyl)morpholine-4-carboxylate (commercially available, 0.62 g, 2.87 mmol) in dichloromethane (28.0 ml) were added sequentially pyridine (0.5 ml, 5.73 mmol) and acetyl chloride (0.25 ml, 3.44 mmol). After 30 min the reaction was diluted with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride. The resulting mixture was extracted with ethyl acetate (×3), and the combined organic layers were then dried over sodium sulfate, filtered, and concentrated under reduced pressure. The resulting light yellow oil was purified by flash column chromatography (ISCO, SiO2, 0→10% methanol in ethyl acetate over 10 min) to afford (S)-tert-butyl 3-(acetamidomethyl)morpholine-4-carboxylate (0.741 g, yield: almost quantitative, INTERMEDIATE 86A STEP 1).

後処理

  1. extractionThe resulting mixture was extracted with ethyl acetate (×3)
  2. dry with materialthe combined organic layers were then dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting light yellow oil was purified by flash column chromatography (ISCO, SiO2, 0→10% methanol in ethyl acetate over 10 min)

出典と根拠

ORDレコード
ord-9ff96de23ff84d01a6b5490e1521df03
出典データセット
uspto-grants-2016_02
特許番号
US09248140B2

関連ノート

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