Ammonia → (2S)-N-(tert-Butyloxycarbonyl)piperidine-2-carboxamide

HRID 1927802ノート

反応式

HRID 1927802 の反応式
[C:1]([O:5][C:6](N1CCCC[C@H]1C(O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH2:17].O[N:19]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[N:21]=N1.CCN=C=NCCCN(C)C.Cl.N>C(Cl)Cl.CN(C=O)C>[C:1]([O:5][C:6]([NH:19][C:23]([C@@H:24]1[CH2:25][CH2:26][CH2:27][CH2:22][NH:21]1)=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 4

HCID 222AmmoniaHCID 688617(2S)-1-((tert-butoxy)carbonyl)piperidine-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

生成物 1

HCID 51534906(2S)-N-(tert-Butyloxycarbonyl)piperidine-2-carboxamide収率 57%

試薬・触媒・溶媒 1

HCID 22350042dichloromethane N,N-dimethylformamide溶媒

実験手順

(2S)—N-(tert-Butyloxycarbonyl)pipecolinic acid (3.0 g, 13.0 mmol) was dissolved in CH2Cl2/DMF (9:1, 150 ml). To this solution at 0° C. was added 1-hydroxybenzotriazole hydrate (2.0 g, 14.8 mmol) and water soluble carbodiimide (2.74 g, 13.7 mmol). After 1 h at 0° C. ammonia (35%, 25 ml) was added. After 18 h at 0° C. to room temperature the solvent was removed in vacuo and the residue was taken up in ethyl acetate (500 ml). This solution was washed with 0.3M KHSO4, sat. NaHCO3, water and brine, dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash chromatography (eluant: 4% methanol, 96% chloroform) to give a white solid identified as the title compound (1.7 g, 7.4 mmol, 57%).

後処理

  1. customAfter 18 h at 0° C. to room temperature the solvent was removed in vacuo
  2. washThis solution was washed with 0.3M KHSO4, sat. NaHCO3, water and brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated in vacuo
  5. customThe residue was purified by flash chromatography (eluant: 4% methanol, 96% chloroform)
  6. customto give a white solid

出典と根拠

ORDレコード
ord-1697183e0e4d4b59ba5c7d412c9ba43b
出典データセット
uspto-grants-2012_05
特許番号
US08183280B2

反応ノート

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