1,5-Dibromopentane → methyl(S)-3-tert-butoxycarbonylamino-2-piperidin-1-ylpropanoate

HRID 1620376노트

반응식

HRID 1620376 반응식
C(N(CC)CC)C.Cl.[NH2:9][C@@H:10]([CH2:15][NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:11]([O:13][CH3:14])=[O:12].Br[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]Br>C(O)(C)(C)C>[C:20]([O:19][C:17]([NH:16][CH2:15][C@H:10]([N:9]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)[C:11]([O:13][CH3:14])=[O:12])=[O:18])([CH3:23])([CH3:22])[CH3:21]

참가 물질

5

반응물 3

HCID 81001,5-DibromopentaneHCID 8471TriethylamineHCID 18334328methyl (2S)-2-amino-3-{[(tert-butoxy)carbonyl]amino}propanoate hydrochloride

생성물 1

HCID 67056335methyl(S)-3-tert-butoxycarbonylamino-2-piperidin-1-ylpropanoate수율 59.7%

시약·촉매·용매 1

HCID 6386tert-Butanol용매

반응 조건

온도
40 °C

실험 절차

14.4 ml (104 mmol) of triethylamine are added to a solution of 8.0 g (31 mmol) of commercial methyl (S)-2-amino-3-tert-butoxycarbonylaminopropanoate hydrochloride in 160 ml of tert-butanol, and then the reaction medium is stirred for 30 min at 40° C., and filtered in order to remove the triethylammonium salts. 6 ml (44 mmol) of 1,5-dibromopentane are added to the filtrate thus obtained, and the reaction medium is heated at 80° C. for 3 days. After the insoluble material has been filtered off, the filtrate is concentrated under vacuum. The crude residue is purified by chromatography on silica gel, elution being carried out with a 70/30 heptane/ethyl acetate mixture. 5.3 g (59%) of methyl(S)-3-tert-butoxycarbonylamino-2-piperidin-1-ylpropanoate are obtained in the form of a colorless oil.

후처리

  1. filtrationfiltered in order
  2. customto remove the triethylammonium salts
  3. customthus obtained
  4. temperaturethe reaction medium is heated at 80° C. for 3 days
  5. filtrationAfter the insoluble material has been filtered off
  6. concentrationthe filtrate is concentrated under vacuum
  7. customThe crude residue is purified by chromatography on silica gel, elution

출처 및 근거

ORD 기록
ord-3ae1e6cb501e411887a921d4cbe7afb6
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772478B2

반응 노트

불러오는 중…