3,5-Dichlorophenol → n-Tert-butoxycarbonyl-4-(3,5-dichlorophenoxy)piperidine

HRID 2185479ノート

反応式

HRID 2185479 の反応式
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][CH:30]([OH:33])[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21].[Cl:34][C:35]1[CH:36]=[C:37](O)[CH:38]=[C:39]([Cl:41])[CH:40]=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][CH:30]([O:33][C:37]2[CH:36]=[C:35]([Cl:34])[CH:40]=[C:39]([Cl:41])[CH:38]=2)[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:21])[CH3:22]

参加物

6

反応物 4

HCID 115713,5-DichlorophenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

生成物 1

HCID 22458487n-Tert-butoxycarbonyl-4-(3,5-dichlorophenoxy)piperidine収率 78.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Triphenylphosphine (786 mg) was added to a solution of N-tert-butoxycarbonyl-4-hydroxypiperidine (603 mg), 3,5-dichlorophenol (489 mg) and diethyl azodicarboxylate (522 mg) in tetrahydrofuran (15 mL) at room temperature. After stirring at room temperature for 14 hr, the reaction mixture was evaporated in vacuo. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:6) to give the titled compound (815 mg) as a colorless oil: 1H NMR (400 MHz, CDCl3) δ 1.48 (s, 9H), 1.75 (m, 2H), 1.90 (m, 2H), 3.37 (m, 2H), 3.66 (m, 2H), 4.44 (m, 1H), 6.80 (d, J=1.5 Hz, 2H), and 6.95 (s, 1H); mass spectrum (EI+) m/e 345 (M).

後処理

  1. customthe reaction mixture was evaporated in vacuo
  2. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:6)

出典と根拠

ORDレコード
ord-64ab112964fc4ee797f7219fe2037cf1
出典データセット
uspto-grants-2002_06
特許番号
US06399629B1

反応ノート

読み込み中…