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Cesium carbonate → Ethyl (3S)-3-[4-[[4-(spiro[indane-1,4'-piperidine]-1'-ylmethyl)phenyl]methoxy]phenyl]hex-4-ynoate

HRID 390403
ノート
印刷プレビュー

反応式

HRID 390403 の反応式
[NH:1]1[CH2:6][CH2:5][C:4]2([C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:8][CH2:7]2)[CH2:3][CH2:2]1.C([O-])([O-])=O.[Cs+].[Cs+].[CH2:21]([O:23][C:24](=[O:46])[CH2:25][CH:26]([C:30]1[CH:35]=[CH:34][C:33]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][C:41]([CH2:44]Br)=[CH:40][CH:39]=2)=[CH:32][CH:31]=1)[C:27]#[C:28][CH3:29])[CH3:22]>C(#N)C>[N:1]1([CH2:44][C:41]2[CH:40]=[CH:39][C:38]([CH2:37][O:36][C:33]3[CH:34]=[CH:35][C:30]([C@@H:26]([C:27]#[C:28][CH3:29])[CH2:25][C:24]([O:23][CH2:21][CH3:22])=[O:46])=[CH:31][CH:32]=3)=[CH:43][CH:42]=2)[CH2:6][CH2:5][C:4]2([C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:8][CH2:7]2)[CH2:3][CH2:2]1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 156376162,3-Dihydrospiro(indene-1,4'-piperidine)HCID 670873073-[4-(4-Bromomethyl-benzyloxy)-phenyl]-hex-4-ynoic acid ethyl ester

生成物 1

HCID 58230573Ethyl (3S)-3-[4-[[4-(spiro[indane-1,4'-piperidine]-1'-ylmethyl)phenyl]methoxy]phenyl]hex-4-ynoate収率 93.7%

試薬・触媒・溶媒 1

HCID 6342
Acetonitrile
溶媒

実験手順

To a solution of 2,3-dihydrospiro[indene-1,4′-piperidine] (0.37 g, 1.68 mmol) in acetonitrile (20.0 mL), is added Cs2CO3 (1.37 g, 4.21 mmol at room temperature, followed by the addition of 3-[4-(4-bromomethyl-benzyloxy)-phenyl]-hex-4-ynoic acid ethyl ester (0.70 g, 1.68 mmol). The reaction mixture is stirred overnight at room temperature. The reaction mixture is filtered through diatomaceous earth and the filtrate is evaporated. The crude product is purified by silica gel column chromatography (gradient 3% methanol in DCM) to give the title compound as colorless gel, (0.82 g, 93.7%). ESI/MS 522.2 (M+H)+.

後処理

  1. filtrationThe reaction mixture is filtered through diatomaceous earth
  2. customthe filtrate is evaporated
  3. customThe crude product is purified by silica gel column chromatography (gradient 3% methanol in DCM)

出典と根拠

ORDレコード
ord-aaddc74571b04fd2972abedbeb097ddd
出典データセット
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08383642B2

反応ノート

読み込み中…

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