Triethylamine → 2-Propanol, reaction products with ammonia, distn. residues

HRID 1795293ノート

反応式

HRID 1795293 の反応式
[CH:1]1([CH:4]=[O:5])[CH2:3][CH2:2]1.Cl.[CH2:7]([O:14][C:15](=[O:21])[NH:16][CH2:17][CH2:18][CH2:19][NH2:20])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(N(CC)CC)C.[BH4-].[Na+].[OH-].[Na+]>CO.C(Cl)(Cl)Cl>[NH3:16].[CH3:7][CH:4]([OH:5])[CH3:1].[CH2:7]([O:14][C:15](=[O:21])[NH:16][CH2:17][CH2:18][CH2:19][NH:20][CH2:4][CH:1]1[CH2:2][CH2:3]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

参加物

9

反応物 5

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 123114CyclopropanecarboxaldehydeHCID 4311764Sodium borohydrideHCID 13196227Benzyl (3-aminopropyl)carbamate--hydrogen chloride (1/1)

生成物 2

HCID 183319422-Propanol, reaction products with ammonia, distn. residuesHCID 21023628Carbamic acid, [3-[(cyclopropylmethyl)amino]propyl]-, phenylmethyl ester

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6212Chloroform溶媒

実験手順

A solution of cyclopropanecarbaldehyde (4.6 ml, 0.061 mol), (3-amino-propyl)-carbamic acid benzyl ester hydrochloride (15 g, 0.061 mol) and triethylamine (8.5 ml, 0.061 mol) in methanol (244 ml) was stirred at room temperature overnight. Sodium borohydride (3.7 g, 0.098 mol) was added and the reaction mixture was stirred at room temperature for 4 h. Sodium hydroxide solution (1N) was added and the reaction was concentrated to remove methanol. The residue was extracted with ethyl acetate and the combined extracts were washed with brine. Drying and solvent evaporation gave an oil; flash chromatography (silica gel, chloroform saturated with ammonia-2-propanol, 99.5:0.5) gave [3-(cyclopropylmethyl-amino)-propyl]-carbamic acid benzyl ester; 1H NMR (CDCl3, 400 MHz) δ 7.35 (m, 5H), 5.60 (bs, 1H), 5.10 (s, 2H), 3.30 (q, 2H, J=6.1 Hz), 2.70 (t, 2H, J=6.5 Hz), 2.43 (d, 2H, J=6.8 Hz), 1.67 (m, 2H), 0.92 (m, 1H), 0.46 (m, 2H), 0.099 (q, 2H, J=4.9 Hz).

後処理

  1. concentrationthe reaction was concentrated
  2. customto remove methanol
  3. extractionThe residue was extracted with ethyl acetate
  4. washthe combined extracts were washed with brine
  5. customDrying
  6. customsolvent evaporation
  7. customgave an oil

出典と根拠

ORDレコード
ord-481ce3f9039b4baea1007d97b6a1fe70
出典データセット
uspto-grants-2006_04
特許番号
US07026324B2

反応ノート

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