Methyl 2,2-dimethylacetoacetate → Methyl (3R)-3-hydroxy-2,2-dimethylbutanoate

HRID 386896노트

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HRID 386896 반응식
[CH3:1][O:2][C:3](=[O:10])[C:4]([CH3:9])([CH3:8])[C:5](=[O:7])[CH3:6]>CO.C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Ru]Cl>[CH3:1][O:2][C:3](=[O:10])[C:4]([CH3:9])([CH3:8])[C@H:5]([OH:7])[CH3:6]

참가 물질

4

반응물 1

HCID 96925Methyl 2,2-dimethylacetoacetate

생성물 1

HCID 12475664Methyl (3R)-3-hydroxy-2,2-dimethylbutanoate수율 95%

시약·촉매·용매 2

HCID 11136527(R)-[2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl dichlororuthenium촉매HCID 887Methanol용매

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온도
30 °C

실험 절차

The reaction is carried out in a 100-mL autoclave. 2,2-Dimethyl-3-oxo-butyric acid methyl ester (4.0 g, 27.8 mmol) is dissolved in 35 mL of degassed methanol under Argon atomosphere. Dichloro[(R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl]ruthenium (II) (230.0 mg, 0.28 mmol) is added and the reaction mixture is purged with nitrogen twice and once with hydrogen. The autoclave is pressurized with hydrogen to 500 psi and stirred at 30° C. for 40 h. After this time, the reaction mixture is filtered through celite and concentrated under reduced pressure to provide 3.8 g of the title compound as a green oil with ee of 96%. Yield: 95%. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.15 (3H, d, J=6.4 Hz), 1.2 (6H, d, J=5.2 Hz), 2.6 (1H, br. s), 3.7 (3H, s), 3.9 (1H, q, J=6.4 Hz).

후처리

  1. customthe reaction mixture is purged with nitrogen twice
  2. filtrationAfter this time, the reaction mixture is filtered through celite and
  3. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-3c026a91520343239ff5491dacbe8548
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372874B2

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