Allyl bromide → [4-(4-Allyloxyphenyl)butyl]carbamic acid benzyl ester

HRID 25118

反応式

HRID 25118 の反応式
[CH3:1][C:2](C)([O-])[CH3:3].[K+].[C:7]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1)([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8].C(Br)C=C>CC#N.C1OCCOCCOCCOCCOCCOC1>[C:7]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:3][CH:2]=[CH2:1])=[CH:24][CH:23]=1)([O:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:8]

参加物

6

反応物 3

HCID 7841Allyl bromideHCID 11637991N-Cbz4-(4-hydroxyphenyl)butylamineHCID 23665647Potassium tert-butoxide

生成物 1

HCID 11551825[4-(4-Allyloxyphenyl)butyl]carbamic acid benzyl ester収率 71%

試薬・触媒・溶媒 2

HCID 2855718-Crown-6触媒HCID 6342Acetonitrile溶媒2 回

実験手順

Potassium tert-butoxide (1.7 g, 15.2 mmol) and 18-crown-6 (0.1 g, 0.3 mmol) were added to a solution of 29 (4.3 g, 14.3 mmol) in dry MeCN (80 mL) and the mixture was stirred for 20 min at room temperature. After this time, allyl bromide (1.2 mL, 14.3 mmol) in MeCN (10 mL) was added. The reaction mixture was stirred overnight at room temperature, then the precipitate was filtered off and washed with ethyl acetate. The organic fractions were combined, the solvent was removed at reduced pressure and the residue was purified twice by flash chromatography (silica gel, 1:1 ethyl acetate/hexanes) to provide compound 30 (3.4 g, 71%) as a white solid. 1H NMR (300 MHz, CDCl3) δ 1.55 (m, 4H), 2.54 (t, 2H), 3.20 m, 2H), 4.50 (d, 2H), 5.08 (s, 2H), 5.28 (d, 1H), 5.40 (d, 1H), 6.06 (m, 1H), 6.82 (d, 2H), 7.05 (d, 2H), 7.33 (s, 5H).

後処理

  1. stirringThe reaction mixture was stirred overnight at room temperature
  2. filtrationthe precipitate was filtered off
  3. washwashed with ethyl acetate
  4. customthe solvent was removed at reduced pressure
  5. customthe residue was purified twice by flash chromatography (silica gel, 1:1 ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-b5691c73bf6147188819ae0d3a31163c
出典データセット
uspto-grants-2005_02
特許番号
US06858615B2

関連ノート

読み込み中…