Methyl iodide → Exo-8-boc-8-azabicyclo[3.2.1]octane-3-carboxylic acid methyl ester

HRID 537122노트

반응식

HRID 537122 반응식
[C:1]([O:5][C:6]([N:8]1[C@H:13]2[CH2:14][CH2:15][C@@H:9]1[CH2:10][CH:11]([C:16]([OH:18])=[O:17])[CH2:12]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:19](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O.C(OCC)(=O)C>[C@@H:13]12[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[C@@H:9]([CH2:15][CH2:14]1)[CH2:10][CH:11]([C:16]([O:18][CH3:19])=[O:17])[CH2:12]2

참가 물질

6

반응물 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 50999080exo-8-Boc-8-azabicyclo(3.2.1)octane-3-carboxylic acid

생성물 1

HCID 67491395Exo-8-boc-8-azabicyclo[3.2.1]octane-3-carboxylic acid methyl ester수율 92.1%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of (1R,5S)-8-(tert-butoxycarbonyl)-8-azabicyclo[3.2.1]octane-3-carboxylic acid (500 mg, 1.96 mmol) in N,N-dimethylformamide (5 mL) was added potassium carbonate (541 mg, 3.92 mmol) and methyl iodide (0.18 mL, 2.94 mmol). The reaction was stirred at room temperature for 18 hours. The reaction was diluted with ethyl acetate (50 mL) and heptanes (50 mL), and then washed with water (100 mL) and brine (50 mL). The organics were dried over sodium sulfate, filtered, and concentrated. Purification by flash column chromatography gave the title compound (486 mg, 92%) as a clear oil. 1H NMR (400 MHz, CDCl3, δ): 4.17-4.29 (m, 2H), 3.65 (s, 3H), 2.75-2.86 (m, 1H), 1.93-2.01 (m, 2H), 1.79-1.92 (m, 2H), 1.67-1.76 (m, 2H), 1.58-1.66 (m, 2H), 1.45 (s, 9H).

후처리

  1. washwashed with water (100 mL) and brine (50 mL)
  2. dry with materialThe organics were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by flash column chromatography

출처 및 근거

ORD 기록
ord-bcc69acaeca941248ed62ba0c8ef6e86
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859773B2

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