(4R,5R)-3-Methoxyamino-4,5-dimethyl-(Z)-oct-2-enoic Acid Ethyl Ester → (4R,5R)-3-Amino-4,5-dimethyl-(Z)-oct-2-enoic Acid Ethyl Ester

HRID 349848ノート

反応式

HRID 349848 の反応式
[CH2:1]([O:3][C:4](=[O:17])/[CH:5]=[C:6](\[NH:14]OC)/[C@H:7]([CH3:13])[C@H:8]([CH3:12])[CH2:9][CH2:10][CH3:11])[CH3:2].[H][H]>[Ni].CO>[CH2:1]([O:3][C:4](=[O:17])/[CH:5]=[C:6](\[NH2:14])/[C@H:7]([CH3:13])[C@H:8]([CH3:12])[CH2:9][CH2:10][CH3:11])[CH3:2]

参加物

5

反応物 2

HCID 86597973(4R,5R)-3-Methoxyamino-4,5-dimethyl-(Z)-oct-2-enoic Acid Ethyl EsterHCID 178418361HCID 178418361、化合物

生成物 1

HCID 86597974(4R,5R)-3-Amino-4,5-dimethyl-(Z)-oct-2-enoic Acid Ethyl Ester収率 100.1%

試薬・触媒・溶媒 2

HCID 935Nickel触媒2 回HCID 887Methanol溶媒

実験手順

A reactor vessel charged with 171 g of (4R,5R)-3-methoxyamino-4,5-dimethyl-(Z)-oct-2-enoic acid ethyl ester, 1600 mL of MeOH, and 65 g of Raney nickel (Ra—Ni) catalyst. The methoxyamino ester was reacted with hydrogen at 50 psig to 55 psig. During the hydrogenation, additional Ra—Ni was added at reaction times of 8 hours (20 g), 21 hours (20 g), and 37 hours (8 g). After the reaction was completed (51 hours), the Ra—Ni was filtered off and the filtrate was concentrated under reduced pressure to give 150 g (>99% yield) of the titled compound as an oil: 1H NMR (400 MHz, CHLOROFORM-D): 0.86 (t, J=4.5 Hz, 3 H), 0.88 (d, J=4.9 Hz, 3 H), 1.05–1.50 (m, 6 H), 1.10 (d, J=7.0 Hz, 3 H), 1.24 (t, J=7.2 Hz, 3 H), 1.87 (m, 1 H), 3.45 (s, 2 H) 4.08 (q, J=7.0 Hz, 2 H).

後処理

  1. custom(51 hours)
  2. filtrationthe Ra—Ni was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-a6c455ffa11c4d8cbebca4ef2092c804
出典データセット
uspto-grants-2007_02
特許番号
US07179934B2

反応ノート

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