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

HRID 1777268ノート

反応式

HRID 1777268 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 49%

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒

反応条件

温度
40 °C

実験手順

1.8 ml (6.5 mmol) of triethylamine are added to a solution of 1 g (6.5 mmol) of commercial methyl (S)-2-amino-3-tert-butoxycarbonylaminopropanoate hydrochloride in 20 ml of tert-butanol. The reaction medium is stirred for 30 min at 40° C. then filtered. Added to the filtrate thus obtained are 1.2 ml (8.6 mmol) of 1,5-dibromopentane and the reaction medium is heated at 60° C. for 3 days. After filtration of the insoluble fraction, the filtrate is concentrated under vacuum. The crude residue is purified by chromatography over silica gel eluted with a 70/30 heptane/ethyl acetate mixture. 600 mg (49%) of methyl (S)-3-tert-butoxycarbonylamino-2-piperidin-1-yl-propanoate are obtained in the form of a colourless oil.

後処理

  1. filtrationthen filtered
  2. additionAdded to the filtrate
  3. customthus obtained
  4. temperaturethe reaction medium is heated at 60° C. for 3 days
  5. filtrationAfter filtration of the insoluble fraction
  6. concentrationthe filtrate is concentrated under vacuum
  7. customThe crude residue is purified by chromatography over silica gel
  8. washeluted with a 70/30 heptane/ethyl acetate mixture

出典と根拠

ORDレコード
ord-40f75cfcc5fc4cbcbb9ab9ce57de8ac0
出典データセット
uspto-grants-2016_02
特許番号
US09266848B2

反応ノート

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