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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
Notes
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Reaction equation

HRID 2165142 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-67424a3223d64bca82271d6936db79a1
Source dataset
uspto-grants-1990_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04939143

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes