Sodium hydride → Ethyl 5-methoxy-1-oxo-1,3-dihydrospiro[indene-2,4'-piperidine]-1'-carboxylate

HRID 713403ノート

反応式

HRID 713403 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6]2.[CH2:13]([O:15][C:16](=[O:24])[N:17]([CH2:21][CH2:22]Br)[CH2:18][CH2:19]Br)[CH3:14].[H-].[Na+]>CN(C=O)C.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[C:7]1([CH2:22][CH2:21][N:17]([C:16]([O:15][CH2:13][CH3:14])=[O:24])[CH2:18][CH2:19]1)[CH2:6]2

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 787875-Methoxyindan-1-oneHCID 10924683Ethyl bis(2-bromoethyl)carbamate

生成物 1

HCID 71227303Ethyl 5-methoxy-1-oxo-1,3-dihydrospiro[indene-2,4'-piperidine]-1'-carboxylate収率 31.5%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

To a stirred solution of 5-methoxy-1-indanone (1.0 g, 6.17 mmol) and bis-(2-bromo-ethyl)-carbamic acid ethyl ester (1.87 g, 6.17) in DMF (10 mL) at 50° C. was added NaH (0.370 g, 15.4 mmol) by small portions. After being stirred at 50° C. for 16 hr, the reaction was cooled to ambient temperature. The reaction was diluted with 15 mL of ethyl acetate and washed twice with 10 mL of water, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by flash column (gradient of 85:15 to 60:40 heptane/ethyl acetate over 30 min) to give the title compound (590 mg, 1.945 mmol). MS calculated for C17H22NO4 304.4. found (ESI) m/z 304.2 (M+H)+, retention time 1.56 min.

後処理

  1. temperaturethe reaction was cooled to ambient temperature
  2. washwashed twice with 10 mL of water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by flash column (gradient of 85:15 to 60:40 heptane/ethyl acetate over 30 min)

出典と根拠

ORDレコード
ord-43c8330ffbaa4b3ab83710c9a5301053
出典データセット
uspto-grants-2015_11
特許番号
US09181266B2

反応ノート

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