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Ammonium Chloride → Racemic 3-[1-aminomethyl-5-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-pentyl]-6-chloro-1,3-dihydro-indol-2-one

HRID 2065417
ノート
印刷プレビュー

反応式

HRID 2065417 の反応式
[C:1]([Si:5]([CH3:30])([CH3:29])[O:6][CH2:7][CH2:8][C:9]([CH3:28])([CH3:27])[CH2:10][CH:11]([CH:16]1[C:24]2[C:19](=[CH:20][C:21]([Cl:25])=[CH:22][CH:23]=2)[NH:18][C:17]1=[O:26])[CH2:12][N+:13]([O-])=O)([CH3:4])([CH3:3])[CH3:2].[Cl-].[NH4+]>CO.[Zn]>[NH2:13][CH2:12][CH:11]([CH:16]1[C:24]2[C:19](=[CH:20][C:21]([Cl:25])=[CH:22][CH:23]=2)[NH:18][C:17]1=[O:26])[CH2:10][C:9]([CH3:28])([CH3:27])[CH2:8][CH2:7][O:6][Si:5]([C:1]([CH3:2])([CH3:3])[CH3:4])([CH3:30])[CH3:29]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 25517Ammonium ChlorideHCID 58399000Racemic 3-[5-(tert-butyl-dimethyl-silanyloxy)-3,3-dim ethyl-1-nitromethyl-pentyl]-6-chloro-1,3-dihydro-indol-2-one

生成物 1

HCID 58398996Racemic 3-[1-aminomethyl-5-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-pentyl]-6-chloro-1,3-dihydro-indol-2-one収率 86%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒
HCID 887
Methanol
溶媒

実験手順

To a solution of racemic 3-[5-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-1-nitromethyl-pentyl]-6-chloro-1,3-dihydro-indol-2-one (0.5 g, 1.1 mmol) in methanol (20 mL) was added an aqueous solution (5 mL) of ammonium chloride (0.6 g, 11 mmol), followed by the addition of Zinc (Aldrich, activated) (0.7 g, 11 mmol). The reaction mixture was stirred at room temperature for 2 h. The mixture was filtered through a short pad of celite. The filtrate was concentrated to a small volume, then the residue was partitioned between ethyl acetate and water. The organic layer was separated, the aqueous layer was extracted with ethyl acetate. The organic layers were combined, washed with saturated aqueous NaHCO3, brine, dried over MgSO4, and concentrated to give racemic 3-[1-aminomethyl-5-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-pentyl]-6-chloro-1,3-dihydro-indol-2-one as a white foam (0.4 g, 86%)

後処理

  1. filtrationThe mixture was filtered through a short pad of celite
  2. concentrationThe filtrate was concentrated to a small volume
  3. customthe residue was partitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. washwashed with saturated aqueous NaHCO3, brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-31ee84f9591544d19adf5947e920149f
出典データセット
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08288431B2

反応ノート

読み込み中…

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