Isopropyl iodide → (+/-)-cis-1-Methylethyl 6-(cyanomethyl)-2,2-dimethyl-1,3-dioxane4-acetate

HRID 5688

반응식

HRID 5688 반응식
[C:1]([CH2:3][C@H:4]1[O:9][C:8]([CH3:11])([CH3:10])[O:7][C@@H:6]([CH2:12][C:13]([OH:15])=[O:14])[CH2:5]1)#[N:2].N12CCCN=C1CC[CH2:19][CH2:18][CH2:17]2.IC(C)C>C(#N)C.C(OCC)C>[C:1]([CH2:3][C@H:4]1[O:9][C:8]([CH3:11])([CH3:10])[O:7][C@@H:6]([CH2:12][C:13]([O:15][CH:18]([CH3:19])[CH3:17])=[O:14])[CH2:5]1)#[N:2]

참가 물질

6

반응물 3

HCID 6362Isopropyl iodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10976794[(4R,6R)-6-(Cyanomethyl)-2,2-dimethyl-1,3-dioxan-4-yl]acetic acid

생성물 1

HCID 10999646(+/-)-cis-1-Methylethyl 6-(cyanomethyl)-2,2-dimethyl-1,3-dioxane4-acetate

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6342Acetonitrile용매

실험 절차

To a solution of (±)-cis-6-(cyanomethyl)-2,2-dimethyl-1,3-dioxane-4-acetic acid, 0.6 g (3 mmol), in acetonitrile, 2 mL, is added 1,8-diazabicyclo[5.4.0]-undec-7-ene (DBU), 0.45 mL (3 mmol), and 2-iodopropane, 0.33 mL (3.3 mmol). The solution is stirred overnight at room temperature, diluted with diethyl ether, washed with brine, and dried (magnesium sulfate). Flash chromatography provides 0.55 g of (±)-cis-1-methylethyl 6-(cyanomethyl)-2,2-dimethyl-1,3-dioxane-4-acetate.

후처리

  1. washwashed with brine
  2. dry with materialdried (magnesium sulfate)

출처 및 근거

ORD 기록
ord-3e866dd73b724ce1babaa729046e5dfa
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05245047

연결된 노트

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