(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 132667노트

반응식

HRID 132667 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 935Nickel촉매2회HCID 887Methanol용매

실험 절차

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, 3H), 0.88 (d, J=4.9 Hz, 3H), 1.05-1.50 (m, 6H), 1.10 (d, J=7.0 Hz, 3H), 1.24 (t, J=7.2 Hz, 3H), 1.87 (m, 1H), 3.45 (s, 2H) 4.08 (q, J=7.0 Hz, 2H).

후처리

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

출처 및 근거

ORD 기록
ord-d2711d1981f34a77a28ae92641f7c77e
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07388023B2

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