tert-Butanol → Benzyl 4-((tert-butoxycarbonyl)amino)piperidine-1-carboxylate

HRID 369109

反応式

HRID 369109 の反応式
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([N:17]=[C:18]=[O:19])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]([OH:24])([CH3:23])([CH3:22])[CH3:21]>CN(C=O)C.O>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([NH:17][C:18]([O:24][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:19])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 2

HCID 6386tert-ButanolHCID 2776273Benzyl 4-isocyanatopiperidine-1-carboxylate

生成物 1

HCID 21981786Benzyl 4-((tert-butoxycarbonyl)amino)piperidine-1-carboxylate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回

実験手順

A solution of 3.2 g (12.3 mmol) of (1-benzyloxycarbonyl-piperidin-4-yl)isocyanate from Step A in 25 mL of DMF was slowly added to a suspension of CuCl3 in 25 mL of DMF and 12 mL of t-butanol. The reaction was stirred for 24 h and then diluted with water and extracted twice with 1:1 ether:ethyl acetate. The organic layers were each washed with a portion of water and brine, dried over sodium sulfate, combined and concentrated. The residue was purified by FCC eluting with 20% ethyl acetate/hexanes to afford 685 mg of title compound. 1H NMR (400 MHz, CDCl3): δ 1.26 (m, 2H), 1.42 (s, 9H), 1.90 (br d, J=12, 2H), 2.90 (br t, 2H), 3.58 (m, 1H), 4.08 (m, 2H), 4.42 (br s, 1H), 5.09 (s, 2H), 7.33 (m, 5H).

後処理

  1. extractionextracted twice with 1:1 ether
  2. washeach washed with a portion of water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by FCC
  6. washeluting with 20% ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-8651c1513239487a811903cddabdca10
出典データセット
uspto-grants-2000_10
特許番号
US06136827

関連ノート

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