Triethylamine → Benzyl 2-[4-(tert-butoxycarbonylamino)piperidin-1-yl]ethylcarbamate

HRID 1169404ノート

反応式

HRID 1169404 の反応式
Br[CH2:2][CH2:3][NH:4][C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(O)=O.[NH:18]1[CH2:23][CH2:22][CH:21]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:20][CH2:19]1.C(N(CC)CC)C>C(#N)C>[C:27]([O:26][C:25]([NH:24][CH:21]1[CH2:20][CH2:19][N:18]([CH2:2][CH2:3][NH:4][C:5](=[O:14])[O:6][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:23][CH2:22]1)=[O:31])([CH3:30])([CH3:28])[CH3:29]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 278694benzyl N-(2-bromoethyl)carbamateHCID 22990009Tert-butyl 4-piperidinyl-carbamate formic acid salt

生成物 1

HCID 22989976Benzyl 2-[4-(tert-butoxycarbonylamino)piperidin-1-yl]ethylcarbamate収率 77.5%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

Into a solution of 2-bromoethylamine hydrobromide (5.0 g) and potassium carbonate (5.06 g) in THF/water (20/5 ml) was added at 0° C. benzyl chloroformate (4.16 g), and the resulting mixture was stirred at room temperature for 16 hours. The reaction mixture was mixed with water and was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated solution of sodium chloride and was dried with anhydrous magnesium sulfate. The resulting organic layer was evaporated under reduced pressure to obtain benzyl 2-bromoethylcarbamate (7.32 g). A solution of benzyl 2-bromoethylcarbamate (7.23 g), tert-butyl 4-piperidinyl-carbamate formic acid salt (4.63 g) and triethylamine (8 ml) in acetonitrile (30 ml) was heated at reflux for 24 hours. After the reaction mixture was concentrated under reduced pressure, water was added to the residue, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated solution of sodium chloride and was dried with magnesium sulfate. After concentration under reduced pressure, the residue was subjected to purification using column chromatography (ethyl acetate/hexane) to obtain benzyl 2-[4-(tert-butoxycarbonylamino)piperidin-1-yl]ethylcarbamate (5.5 g) as colorless crystals.

後処理

  1. temperatureat reflux for 24 hours
  2. concentrationAfter the reaction mixture was concentrated under reduced pressure, water
  3. additionwas added to the residue
  4. extractionthe resulting mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with an aqueous saturated solution of sodium chloride
  6. dry with materialwas dried with magnesium sulfate
  7. concentrationAfter concentration under reduced pressure
  8. customthe residue was subjected to purification

出典と根拠

ORDレコード
ord-d5a7962d8d364a8b8ee02fad37941f68
出典データセット
uspto-grants-2003_09
特許番号
US06627651B1

反応ノート

読み込み中…