Acetaldehyde, 2,2-dimethoxy- → (R)-N-(2,2-dimethoxyethyl)-3-methylbutan-2-amine

HRID 909872ノート

反応式

HRID 909872 の反応式
[CH3:1][CH:2]([CH3:6])[C@H:3]([NH2:5])[CH3:4].[CH3:7][O:8][CH:9]([O:12][CH3:13])[CH:10]=O>CO.[Pd].O>[CH3:7][O:8][CH:9]([O:12][CH3:13])[CH2:10][NH:5][C@@H:3]([CH:2]([CH3:6])[CH3:1])[CH3:4]

参加物

6

反応物 2

HCID 162650Acetaldehyde, 2,2-dimethoxy-HCID 69997861,2-Dimethylpropylamine, (R)-

生成物 1

HCID 58168508(R)-N-(2,2-dimethoxyethyl)-3-methylbutan-2-amine

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

A solution of (R)-3-methylbutan-2-amine (10.50 g) and 2,2-dimethoxyacetaldehyde (18.18 mL) in methanol (50 mL) was added to palladium on carbon (3 g) in water (3.0 mL) at 25° C. The mixture was hydrogenated under 5 bar at 25° C. for 24 h. The reaction mixture was filtered through Celite and concentrated under vacuum to afford (R)—N-(2,2-dimethoxyethyl)-3-methylbutan-2-amine as a colourless liquid (16.40 g). 1H NMR (300 MHz, CDCl3) δ 4.47 (t, J=5.6 Hz, 1H), 3.39 (s, 6H), 2.77 (dd, J=11.9, 5.4 Hz, 1H), 2.66 (dd, J=11.9, 6.0 Hz, 1H), 2.44 (qd, J=6.4, 5.1 Hz, 1H), 1.75-1.63 (m, 1H), 0.96 (d, J=6.3 Hz, 3H), 0.90 (d, J=6.9 Hz, 3H), 0.86 (d, J=6.9 Hz, 3H).

後処理

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-1a22346b508e44bb8525caf50111fe0f
出典データセット
uspto-grants-2011_09
特許番号
US08017602B2

反応ノート

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