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Triphenylphosphine → Methyl 2-(1-tert-Butoxycarbonylpiperidin-3-ylmethoxy)-4-isopropylbenzoate

HRID 1787899
ノート
印刷プレビュー

反応式

HRID 1787899 の反応式
[CH:1]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([OH:14])[CH:5]=1)([CH3:3])[CH3:2].O[CH2:16][CH:17]1[CH2:22][CH2:21][CH2:20][N:19]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:18]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1.C(Cl)Cl>[C:26]([O:25][C:23]([N:19]1[CH2:20][CH2:21][CH2:22][CH:17]([CH2:16][O:14][C:6]2[CH:5]=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:13]=[CH:12][C:7]=2[C:8]([O:10][CH3:11])=[O:9])[CH2:18]1)=[O:24])([CH3:29])([CH3:27])[CH3:28]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 2763851tert-Butyl 3-(hydroxymethyl)piperidine-1-carboxylateHCID 59745620Methyl 4-Isopropyl-2-hydroxybenzoate

生成物 1

HCID 68573359Methyl 2-(1-tert-Butoxycarbonylpiperidin-3-ylmethoxy)-4-isopropylbenzoate収率 43%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

The methyl 4-isopropyl-2-hydroxybenzoate (4.4 g, 22.7 mmol) was dissolved in THF (100 mL). Then 3-(hydroxy-methyl)-1-tert-butoxycarbonylpiperidine (4.88 g, 22.7 mmol) and triphenylphosphine (7.14 g, 27.24 mmol) were added. The mixture was placed in an ice bath, and then diisopropyl azodicarboxylate (4.59 g, 22.7 mmol) in methylene chloride (15 mL) was added dropwise. The reaction mixture was allowed to warm gradually to room temperature. After 16 h, the solvent was removed under vacuum. The solid residue was subjected directly to flash chromatography on silica (0 to 30% EtOAc in hexane gradient), giving the title compound (3.34 g, 43% yield) as an oil.

後処理

  1. customThe mixture was placed in an ice bath
  2. customthe solvent was removed under vacuum

出典と根拠

ORDレコード
ord-f3d29e400cd341f0b5639776912b6bd4
出典データセット
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07511066B2

反応ノート

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