Potassium Hydroxide → (S)-5-Phenyl-1-(triisopropylsilyl)pent-1-yn-3-ol

HRID 593406노트

반응식

HRID 593406 반응식
[OH-].[K+].[C:3]1([CH2:9][CH2:10][C:11](=[O:24])[C:12]#[C:13][Si:14]([CH:21]([CH3:23])[CH3:22])([CH:18]([CH3:20])[CH3:19])[CH:15]([CH3:17])[CH3:16])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>CC1C=CC(C(C)C)=CC=1.CC1C=CC(S([N-][C@H]([C@@H](N)C2C=CC=CC=2)C2C=CC=CC=2)(=O)=O)=CC=1.Cl[Ru+].C(O)CC>[C:3]1([CH2:9][CH2:10][C@H:11]([OH:24])[C:12]#[C:13][Si:14]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:21]([CH3:22])[CH3:23])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

참가 물질

5

반응물 2

HCID 14797Potassium HydroxideHCID 900322545-Phenyl-1-(triisopropylsilyl)pent-1-yn-3-one

생성물 1

HCID 90032808(S)-5-Phenyl-1-(triisopropylsilyl)pent-1-yn-3-ol

시약·촉매·용매 2

HCID 11974997Chloridoruthenium(1+) [(1S,2S)-2-amino-1,2-diphenylethyl](4-methylbenzene-1-sulfonyl)azanide--1-methyl-4-(propan-2-yl)benzene (1/1/1)촉매HCID 10311-Propanol용매

실험 절차

Following a modified procedure of Trost (Trost, B. M. et al., J. Am. Chem. Soc. 128, 6745-6754 (2006)); Potassium hydroxide (8.5 mg, 0.15 mmol, 1.2 mol %) and RuCl(p-cymene)[(S,S)-Ts-DPEN] (80.7 mg, 0.127 mmol, 1 mol %) were added to) PrOH (110 ml) and the resultant mixture was stirred for 2 min at r.t. 5-Phenyl-1-(triisopropylsilyl)pent-1-yn-3-one 84 (4.0 g, 12.7 mmol, 1 eq.) was added via syringe and the mixture was stirred at r.t. for 45 min. The mixture was concentrated in vacuo to give the crude product. This was purified by column chromatography on silica, eluting with petrol/Et2O (20:1 to 10:1), giving the title product 85 as a clear, colourless oil (4.0 g, 99%). The enantiomeric excess was determined to be 99% via HPLC analysis of its derivative 87. Analytical data consistent with the literature (Trost, B. M. et al., J. Am. Chem. Soc. 128, 6745-6754 (2006)).

후처리

  1. concentrationThe mixture was concentrated in vacuo
  2. customto give the crude product
  3. customThis was purified by column chromatography on silica
  4. washeluting with petrol/Et2O (20:1 to 10:1)

출처 및 근거

ORD 기록
ord-7d3f6702dcec485a92774ca78c2186ad
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242954B2

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