Ethanol → tert-butyl N-[(1S,2R)-2-(methylamino)cyclohexyl]carbamate

HRID 1526255ノート

反応式

HRID 1526255 の反応式
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]1[NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12].[CH2:16](O)C.N1(CO)C2C=CC=CC=2N=N1.[BH4-].[Na+]>C(OCC)(=O)C>[CH3:16][NH:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]1[NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13]

参加物

6

反応物 4

HCID 702EthanolHCID 2241691H-Benzotriazole-1-methanolHCID 1514389(1S,2R)-Cyclohexane-1,2-diamine, N1-BOC protectedHCID 4311764Sodium borohydride

生成物 1

HCID 58822134tert-butyl N-[(1S,2R)-2-(methylamino)cyclohexyl]carbamate

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

To a mixture of tert-butyl [(1S,2R)-2-aminocyclohexyl]carbamate (500 mg) and ethanol (10 mL) was added 1H-benzotriazol-1-yl methanol (350 mg), followed by stirring at room temperature for 7 hours. Sodium borohydride (180 mg) was added thereto under ice-cooling, followed by stirring at room temperature for 15 hours. To the reactant were added ethyl acetate and a saturated aqueous sodium hydrogen carbonate solution, followed by liquid separation. The organic phase was dried over anhydrous magnesium sulfate and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent; chloroform:methanol:28% aqueous ammonia=1:0:0-190:9:1) to obtain tert-butyl [(1S,2R)-2-(methylamino)cyclohexyl]carbamate (174 mg) as a pale yellow oily material.

後処理

  1. temperatureunder ice-cooling
  2. stirringby stirring at room temperature for 15 hours
  3. customa saturated aqueous sodium hydrogen carbonate solution, followed by liquid separation
  4. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (eluent; chloroform:methanol:28% aqueous ammonia=1:0:0-190:9:1)

出典と根拠

ORDレコード
ord-5bbf4a26e81a441382d4159180947d66
出典データセット
uspto-grants-2015_07
特許番号
US09085540B2

反応ノート

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