Dicyclohexylcarbodiimide → (RS)-2-(5-Phenyl-[1,3,4]oxadiazol-2-ylmethyl)-piperidine-1-carboxylic acid tert butyl ester

HRID 549317

反応式

HRID 549317 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][C:15]([OH:17])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(N=C=NC2CCCCC2)CCCCC1.[C:33]1([C:39]2NN=[N:41][N:40]=2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C1(C)C=CC=CC=1.C(OCC)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][C:15]1[O:17][C:39]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[N:40][N:41]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

参加物

6

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 50585361-Boc-2-Piperidineacetic AcidHCID 178418369HCID 178418369、化合物

生成物 1

HCID 86628996(RS)-2-(5-Phenyl-[1,3,4]oxadiazol-2-ylmethyl)-piperidine-1-carboxylic acid tert butyl ester収率 64.1%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 3283Diethyl Ether溶媒

反応条件

温度
100 °C

実験手順

A mixture of 2-carboxymethyl-piperidine-1-carboxylic acid tert butyl ester (1.22 g), (Peschke, Bernd, Ankersen, Michael; Hansen, Birgit Sehested; Hansen, Thomas Kruse; Johansen, Nils Langeland, Lau, Jesper; Madsen, Kjeld, Petersen, Hans; Thogersen, Henning; Watson, Brett. Eur. J. Med. Chem. (1999), 34(5), 363-380), dicyclohexylcarbodiimide (1.05 g) and 5-phenyltetrazole (0.73 g) in toluene (25 ml) was heated at 100° C. for 3 h. The reaction mixture was cooled to room temperature, diluted with diethyl ether and solvent decanted from the precipitated gum. The gum was column chromatographed (silica gel, 0-50% ethyl acetate in pentane eluant) to give the title compound (1.1 g).

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customdecanted from the precipitated gum
  3. customchromatographed (silica gel, 0-50% ethyl acetate in pentane eluant)

出典と根拠

ORDレコード
ord-adbfd1b97f7246b9a1edc3c760383e5c
出典データセット
uspto-grants-2011_05
特許番号
US07943645B2

関連ノート

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