Sodium borohydride → 4-[2-(Tert-butyl-diphenyl-silanyloxy)-ethyl]-1-(4-methyl-benzyl)-3-propyl-1,3-dihydro-imidazol-2-one

HRID 1985218

反応式

HRID 1985218 の反応式
[C:1]([Si:5]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[O:6][CH2:7][CH2:8][CH:9]1[N:13]([CH2:14][CH2:15][CH3:16])[C:12](=[O:17])[N:11]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)[C:10]1=O)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CCO>[C:1]([Si:5]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[O:6][CH2:7][CH2:8][C:9]1[N:13]([CH2:14][CH2:15][CH3:16])[C:12](=[O:17])[N:11]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)[CH:10]=1)([CH3:2])([CH3:3])[CH3:4]

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 577192585-[2-(Tert-butyl-diphenyl-silanyloxy)-ethyl]-3-(4-methyl-benzyl)-1-propyl-imidazolidine-2,4-dione

生成物 1

HCID 688674574-[2-(Tert-butyl-diphenyl-silanyloxy)-ethyl]-1-(4-methyl-benzyl)-3-propyl-1,3-dihydro-imidazol-2-one収率 117.8%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of 5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-(4-methyl-benzyl)-1-propyl-imidazolidine-2,4-dione (14.71 g, 27.8 mmol) in EtOH (500 mL) was treated with sodium borohydride (15.78 g, 0.417 mol) in three portions over 6 h and stirred at room temperature under N2 for an additional 16 h. The thick reaction mixture was cooled in an ice bath and slowly quenched with aqueous 1 N HCl (˜1 L) over a 1 h period. The reaction mixture was then worked up extractively with EtOAc, water and brine and the organic layer dried (MgSO4) and the solvent removed in vacuo to give 16.79 g crude 4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-1-(4-methyl-benzyl)-3-propyl-1,3-dihydro-imidazol-2-one that was de-silylated immediately.

後処理

  1. temperatureThe thick reaction mixture was cooled in an ice bath
  2. customslowly quenched with aqueous 1 N HCl (˜1 L) over a 1 h period
  3. dry with materialthe organic layer dried (MgSO4)
  4. customthe solvent removed in vacuo

出典と根拠

ORDレコード
ord-95115b02244b4a48865543f5d38abf1a
出典データセット
uspto-grants-2009_06
特許番号
US07544812B2

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