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

HRID 1620376ノート

反応式

HRID 1620376 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒

反応条件

温度
40 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3ae1e6cb501e411887a921d4cbe7afb6
出典データセット
uspto-grants-2014_07
特許番号
US08772478B2

反応ノート

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