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

HRID 537122ノート

反応式

HRID 537122 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-bcc69acaeca941248ed62ba0c8ef6e86
出典データセット
uspto-grants-2014_10
特許番号
US08859773B2

反応ノート

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