Sodium Iodide → [4-(7,8-Dimethoxy-1-oxo-2,2a,4,5-tetrahydro-1H-3-aza-acenaphthylen-3-yl)-butyl]-carbamic acid tert-butyl ester

HRID 1988118ノート

反応式

HRID 1988118 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:16]3[CH:9]([CH2:10][C:11](=[O:17])[C:12]=3[C:13]=1[O:14][CH3:15])[NH:8][CH2:7][CH2:6]2.C([O-])([O-])=O.[K+].[K+].[Na+].[I-].[C:26]([O:30][C:31](=[O:38])[NH:32][CH2:33][CH2:34][CH2:35][CH2:36]Br)([CH3:29])([CH3:28])[CH3:27]>CN(C=O)C.C(OCC)(=O)C.O>[C:26]([O:30][C:31](=[O:38])[NH:32][CH2:33][CH2:34][CH2:35][CH2:36][N:8]1[CH2:7][CH2:6][C:5]2[C:16]3[CH:9]1[CH2:10][C:11](=[O:17])[C:12]=3[C:13]([O:14][CH3:15])=[C:3]([O:2][CH3:1])[CH:4]=2)([CH3:29])([CH3:28])[CH3:27]

参加物

8

反応物 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 10868765tert-butyl N-(4-bromobutyl)carbamateHCID 577290647,8-Dimethoxy-2a,3,4,5-tetrahydro-2H-3-aza-acenaphthylen-1-one

生成物 1

HCID 57729072[4-(7,8-Dimethoxy-1-oxo-2,2a,4,5-tetrahydro-1H-3-aza-acenaphthylen-3-yl)-butyl]-carbamic acid tert-butyl ester収率 45%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Over a suspension of 7,8-Dimethoxy-2a,3,4,5-tetrahydro-2H-3-aza-acenaphthylen-1-one (0.950 g, 4.1 mmol), K2CO3 (1.89 g, 13.6 mmol) and NaI (0.061 g, 0.4 mmol) in DMF (20 ml) is slowed added (4-Bromo-butyl)-carbamic acid tert-butyl ester (1.09 g, 4.32 mmol) and the mixture is stirred overnight. Then, water (40 ml) and ethyl acetate (40 ml) are added and the layers are separated. The aqueous phase is extracted with ethyl acetate (2×40 ml). The organic layers are collected and washed with water (3×40 ml). After drying with Na2SO4, filtration and vacuum concentration, a brown oil is obtained, which is purified by silicagel chromatography using a gradient of CH2Cl2/methanol (from 100% to 98% CH2Cl2) to obtain a brown solid (0.730 g, 45% yield)

後処理

  1. customthe layers are separated
  2. extractionThe aqueous phase is extracted with ethyl acetate (2×40 ml)
  3. customThe organic layers are collected
  4. washwashed with water (3×40 ml)
  5. dry with materialAfter drying with Na2SO4, filtration and vacuum concentration
  6. customa brown oil is obtained
  7. customwhich is purified by silicagel chromatography

出典と根拠

ORDレコード
ord-10329b214e8c4c7994c7ecb739fde7d7
出典データセット
uspto-grants-2009_06
特許番号
US07553965B2

反応ノート

読み込み中…