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

HRID 1169404

반응식

HRID 1169404 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d5a7962d8d364a8b8ee02fad37941f68
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06627651B1

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