Sodium Azide → tert-Butyl 3-(azidomethyl)piperidine-1-carboxylate

HRID 896511ノート

反応式

HRID 896511 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14]OS(C)(=O)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:20]=[N+:21]=[N-:22].[Na+]>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][N:20]=[N+:21]=[N-:22])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 33557Sodium AzideHCID 22647269tert-Butyl 3-(((methylsulfonyl)oxy)methyl)piperidine-1-carboxylate

生成物 1

HCID 22647380tert-Butyl 3-(azidomethyl)piperidine-1-carboxylate収率 98.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

A solution of 3-methanesulfonyloxymethylpiperidine-1-carboxylic acid tert-butyl ester (19.11 g, 65.1 mmol) in N,N-dimethylformamide (125 mL) was treated with sodium azide (12.70 g, 195 mmol) and the mixture was stirred at 50° C. for 22 hours. The mixture was cooled and filtered, and the filtrate was concentrated under vacuum. The residue was dissolved in ethyl acetate, washed with water, dried over sodium sulfate, and concentrated under vacuum to provide a colorless liquid (15.34 g, 98%) which was used without further purification. 1H NMR (300 MHz, CDCl3) δ3.95 (bd, J=12 Hz, 1H), 3.86 (dt, J=13, 4 Hz, 1H), 3.22 (d, J=7 Hz, 2H), 2.87 (ddd, J=14, 11, 3 Hz, 1H), 2.68 (m, 1H), 1.9-1.6 (3H), 1.49 (m, 1H), 1.47 (s, 9H), 1.26 (m, 1H).

後処理

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated under vacuum
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-43f9ce1bc4a74c4cbd651f79cf06b34c
出典データセット
uspto-grants-2005_07
特許番号
US06919356B2

反応ノート

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