2-Methylbutanoic Acid → Tert-butyl (1-(2-methylbutanoyl)piperidin-4-yl)carbamate

HRID 574685

反応式

HRID 574685 の反応式
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:3][CH2:2]1.CN(C1CCNCC1)C.CCN=C=NCCCN(C)C.[CH3:35][CH:36]([CH2:40][CH3:41])[C:37](O)=[O:38]>C(Cl)Cl>[CH3:35][CH:36]([CH2:40][CH3:41])[C:37]([N:1]1[CH2:2][CH2:3][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])[CH2:5][CH2:6]1)=[O:38]

参加物

6

反応物 4

HCID 83142-Methylbutanoic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 417391N,N-Dimethylpiperidin-4-amineHCID 7238334-(N-Boc-amino)piperidine

生成物 1

HCID 89737189Tert-butyl (1-(2-methylbutanoyl)piperidin-4-yl)carbamate収率 92%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

tert-butyl piperidin-4-ylcarbamate (1 g, 5 mmol), 4-(N,N-dimethylamino)piperidine (0.73 g, 6 mmol) and EDCI (1.15 g, 6 mmol) were added into a solution of 2-methylbutanoic acid (0.612 g, 6 mmol) in CH2Cl2 (200 mL). The reaction was stirred overnight at rt. The reaction was quenched with the addition of 0.1 M HCl. The organic layer was further washed with sat. NaHCO3 solution followed by sat. NaCl solution. The organic layers was concentrated under vacuo. The product was purified by flash chromatography (Hex:EtOAc/1:1) yielding final product 15 (1.3 g, 4.6 mmol, 91.5% yield). H-NMR (DMSO-d6) ∂ 0.79 (q, J=5 Hz, 3H), 0.95 (m, 3H), 1.2-1.3 (m, 2H), 1.38 (s, 9H), 1.50 (m, 2H), 1.73 (t, J=15 Hz, 1H), 2.6-2.7 (m, 2H), 3.06 (t, J=12 Hz, 1H), 3.46 (m, 1H), 3.88 (d, J=12 Hz, 1H), 4.26 (m, 1H), 6.85 (d, J=8 Hz, 1H).

後処理

  1. customThe reaction was quenched with the addition of 0.1 M HCl
  2. washThe organic layer was further washed with sat. NaHCO3 solution
  3. concentrationThe organic layers was concentrated under vacuo
  4. customThe product was purified by flash chromatography (Hex:EtOAc/1:1)

出典と根拠

ORDレコード
ord-a636487e83824fb9bc194a8924aed8c5
出典データセット
uspto-grants-2015_05
特許番号
US09034903B2

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