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Triphenylphosphine → n-Tert-butoxycarbonyl-4-(2-chloro-5-methylphenoxy)piperidine

HRID 2185484
ノート
印刷プレビュー

反応式

HRID 2185484 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:40]=[CH:39][C:38]([CH3:41])=[CH:37][C:36]=1O.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:36]2[CH:37]=[C:38]([CH3:41])[CH:39]=[CH:40][C:35]=2[Cl:34])[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:21])[CH3:22]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 120082-Chloro-5-methylphenolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

生成物 1

HCID 22458419n-Tert-butoxycarbonyl-4-(2-chloro-5-methylphenoxy)piperidine収率 50.1%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

実験手順

Triphenylphosphine (786 mg) was added to a solution of N-tert-butoxycarbonyl-4-hydroxypiperidine (603 mg), 2-chloro-5-methylphenol (428 mg) and diethyl azodicarboxylate (522 mg) in tetrahydrofuran (10 mL) at room temperature. After stirring at room temperature for 18 hr, the reaction mixture was evaporated in vacuo. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:6, v/v) to give the titled compound (489 mg) as a colorless oil: 1H NMR (400 MHz, CDCl3) δ 1.46 (s, 9H), 1.84 (m, 4H), 2.28 (s, 3H), 3.44 (m, 2H), 3.65 (ddd, J=4.0, 8.0, 12.7 Hz, 2H), 4.49 (m, 1H), 6.69 (d, J=8.0 Hz, 1H), 6.75 (s, 1H), and 7.19 (d, J=8.0 Hz, 1H).

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, v/v)

出典と根拠

ORDレコード
ord-de6af0a4d35849e7b81b749235b136df
出典データセット
uspto-grants-2002_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06399629B1

反応ノート

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