Acetic Acid → Tert-butyl 3-(diethylamino)benzylcarbamate

HRID 2071003ノート

反応式

HRID 2071003 の反応式
[CH:1](=O)[CH3:2].[NH2:4][C:5]1[CH:6]=[C:7]([CH:17]=[CH:18][CH:19]=1)[CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13].[BH3-]C#N.[Na+].[CH3:24][C:25](O)=O>CC#N.O>[CH2:24]([N:4]([CH2:1][CH3:2])[C:5]1[CH:6]=[C:7]([CH:17]=[CH:18][CH:19]=1)[CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH3:25]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 5003444Sodium cyanoborohydrideHCID 10775412tert-butyl N-((3-aminophenyl)methyl)carbamate

生成物 1

HCID 68671365Tert-butyl 3-(diethylamino)benzylcarbamate収率 77%

試薬・触媒・溶媒 1

HCID 18373917Acetonitrile--water (1/1)溶媒

反応条件

温度
0 °C

実験手順

Acetaldehyde (0.52 ml, 0.4 g, 9.08 mmol, 5 eq) was added to a stirred solution of tert-butyl 3-aminobenzylcarbamate (derived from 3-(aminomethyl)aniline (TCI America)) in 11 ml CH3CN/H2O (10:1) at 0° C. After 5 min NaBH3CN (0.3 g, 4.54 mmol, 2.5 eq) was added. The reaction was adjusted to pH {tilde over ( )} 7 with HOAc and stirred at 0° C. for 5 min. The ice-bath was removed and the reaction was stirred at room temperature for 45 min. The solvent was removed in vacuo. The residue was diluted with saturated aqueous NaHCO3 and extracted with EtOAc (×2). The combined organics were washed with water (×3), brine (×1), and dried over Na2SO4. The inorganics were filtered off, and the solvent was removed in vacuo. Purification via flash chromatography yielded 0.3875 g (1.4 mmol, 77% yield) of tert-butyl 3-(diethylamino)benzylcarbamate.

後処理

  1. customThe ice-bath was removed
  2. stirringthe reaction was stirred at room temperature for 45 min
  3. customThe solvent was removed in vacuo
  4. additionThe residue was diluted with saturated aqueous NaHCO3
  5. extractionextracted with EtOAc (×2)
  6. washThe combined organics were washed with water (×3), brine (×1)
  7. dry with materialdried over Na2SO4
  8. filtrationThe inorganics were filtered off
  9. customthe solvent was removed in vacuo
  10. customPurification via flash chromatography

出典と根拠

ORDレコード
ord-6923e1b0b96f4fe4a12f762793e92e89
出典データセット
uspto-grants-2012_10
特許番号
US08299267B2

反応ノート

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