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Sodium hydride → Benzyl 3-(3-(tert-butoxycarbonyl)benzyl)-1-cyclohexyl-4-oxo-1,3,8-triazaspiro[4.5]decane-8-carboxylate

HRID 1751019
ノート
印刷プレビュー

反応式

HRID 1751019 の反応式
[H-].[Na+].[CH:3]1([N:9]2[C:13]3([CH2:18][CH2:17][N:16]([C:19]([O:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[O:20])[CH2:15][CH2:14]3)[C:12](=[O:29])[NH:11][CH2:10]2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.Br[CH2:31][C:32]1[CH:33]=[C:34]([CH:42]=[CH:43][CH:44]=1)[C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36]>CN(C)C=O.O>[C:38]([O:37][C:35]([C:34]1[CH:33]=[C:32]([CH:44]=[CH:43][CH:42]=1)[CH2:31][N:11]1[C:12](=[O:29])[C:13]2([CH2:18][CH2:17][N:16]([C:19]([O:21][CH2:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[O:20])[CH2:15][CH2:14]2)[N:9]([CH:3]2[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]2)[CH2:10]1)=[O:36])([CH3:41])([CH3:39])[CH3:40]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 14591193tert-Butyl 3-(bromomethyl)benzoateHCID 58046657Benzyl 1-cyclohexyl-4-oxo-1,3,8-triazaspiro[4.5]decane-8-carboxylate

生成物 1

HCID 58046810Benzyl 3-(3-(tert-butoxycarbonyl)benzyl)-1-cyclohexyl-4-oxo-1,3,8-triazaspiro[4.5]decane-8-carboxylate収率 88%

試薬・触媒・溶媒 2

HCID 962Water
溶媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

Sodium hydride (0.0699 g, 2.91 mol) was added portionwise at 0° C. to benzyl 1-cyclohexyl-4-oxo-1,3,8-triazaspiro[4.5]decane-8-carboxylate (1.03 g, 2.77 mmol) in N,N-dimethylformamide (5 mL) and stirred at 0° C. for 10 minutes. tert-Butyl 3-(bromomethyl)benzoate (0.75 g, 2.77 mmol) was added dropwise at 0° C., the mixture allowed to warm to room temperature, and stirred overnight. The reaction was diluted with water and extracted with ethyl acetate. The extracts were washed with water and brine, dried (MgSO4) and evaporated. The residue was purified by PTLC (50% ethyl acetate/hexanes) to give product as an oil (1.37 g, 88%); 1H NMR (DMSO-d6); δ0.97 (m, 1H); 1.20 (m, 4H); 1.53 (s, 9H); 1.53-1.69 (m, 9H); 2.60 (m, 1H); 3.59 (m, 2H); 3.73 (m, 2H); 4.47 (s, 2H); 5.09 (s, 2H); 7.30-7.39 (m, 5H); 7.45-7.50 (m, 2H); 7.73 (m, 1H); 7.81 (m, 1H); MS for C33H43N3O5 m/z 562 (M+H)+.

後処理

  1. temperatureto warm to room temperature
  2. stirringstirred overnight
  3. extractionextracted with ethyl acetate
  4. washThe extracts were washed with water and brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was purified by PTLC (50% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-d1e1b490367c4ee0a918175896914bc6
出典データセット
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09156840B2

反応ノート

読み込み中…

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