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Oxalic Acid → (E)-3-{2-(4-fluoro-3-methylphenyl)-4-(pyrrolidin-1-yl)-6,6-dimethylcyclohex-1-en-1-yl}propenal

HRID 2165142
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HRID 2165142 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH:12]([N:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)[CH2:11][C:10]([CH3:20])([CH3:19])[C:9]=2[CH:21]=O)=[CH:4][C:3]=1[CH3:23].[Li+].CC([N-]C(C)C)C.C(=NC1CCCCC1)C.[C:41]([OH:46])(=O)[C:42](O)=O>CCOCC.O.C([O-])(O)=O.[Na+]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH:12]([N:14]3[CH2:15][CH2:16][CH2:17][CH2:18]3)[CH2:11][C:10]([CH3:19])([CH3:20])[C:9]=2/[CH:21]=[CH:42]/[CH:41]=[O:46])=[CH:4][C:3]=1[CH3:23]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 971Oxalic AcidHCID 2724682Lithium diisopropylamideHCID 10964544N-cyclohexylethanimineHCID 150569662-(4-Fluoro-3-methylphenyl)-4-(pyrrolidin-1-yl)-6, 6-dimethylcyclohex-1-en-1-carboxaldehyde

생성물 1

HCID 15056967(E)-3-{2-(4-fluoro-3-methylphenyl)-4-(pyrrolidin-1-yl)-6,6-dimethylcyclohex-1-en-1-yl}propenal수율 54.9%

시약·촉매·용매

3
HCID 962Water용매HCID 3283Diethyl Ether용매2회HCID 516892Sodium Bicarbonate용매

실험 절차

In a manner similar to Scheme I, 32 (3.80 g, 12.1 mmol) was treated with the LDA-derived anion of ethylidenecyclohexylamine (2.90 g, 23.2 mmol) in anhydrous ether. Workup and purification of the residue by HPLC using 1% Et3N in 10:1 hexanes:EtOAc as eluent provided the dieneimine (2.4 g). The imine and oxalic acid (10 g) in 40 mL H2O was heated at 100° C. for 2 h, cooled, diluted with saturated NaHCO3 and ether. The organic layer was washed with H2O and brine and dried (MgSO4). Removal of volatiles in vacuo provided 2.27 g of gum which was taken forward without further purification.

후처리

  1. customWorkup and purification of the residue by HPLC
  2. customEtOAc as eluent provided the dieneimine (2.4 g)
  3. temperaturecooled
  4. washThe organic layer was washed with H2O and brine
  5. dry with materialdried (MgSO4)
  6. customRemoval of volatiles in vacuo

출처 및 근거

ORD 기록
ord-67424a3223d64bca82271d6936db79a1
출처 데이터셋
uspto-grants-1990_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04939143

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