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

HRID 1476313노트

반응식

HRID 1476313 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 5234Sodium Chloride용매HCID 6344Dichloromethane용매HCID 516892Sodium Bicarbonate용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-4525b7bc618d412886101f76ffd6f8ed
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09018381B2

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