Heptane → HCID 67032694, compound

HRID 920589Notes

Reaction equation

HRID 920589 reaction equation
[C:1]([O:5][C:6](=[O:32])[CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][O:12][CH:11]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]3[C:28]([Cl:29])=[CH:27][C:26](I)=[CH:25][C:24]=3[Cl:31])=[CH:17][CH:16]=2)[CH2:10]1)([CH3:4])([CH3:3])[CH3:2].[Cl-].[Li+].[CH2:35]([Zn]CC)[CH3:36].CCCCCCC.[NH4+].[Cl-]>C1COCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:1]([O:5][C:6](=[O:32])[CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][O:12][CH:11]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]3[C:28]([Cl:29])=[CH:27][C:26]([CH2:35][CH3:36])=[CH:25][C:24]=3[Cl:31])=[CH:17][CH:16]=2)[CH2:10]1)([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 5

HCID 8900HeptaneHCID 25517Ammonium ChlorideHCID 433294Lithium ChlorideHCID 67033070HCID 67033070, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 67032694HCID 67032694, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

3-{2-[4-(2,6-Dichloro-4-iodo-benzyloxy)-phenyl]-morpholin-4-yl}-propionic acid tert-butyl ester (0.34 g; 0.57 mmol), and Pd(dppf)Cl2 (14.70 mg; 0.02 mmol) were added to a solution of lithium chloride (4.59 ml; 0.50 mol/1; 2.30 mmol) in THF; 0.04 eq.). The resulting mixture was cooled to 0° C. and a solution of diethylzinc in n-heptane (1.15 ml; 1.00 mol/l; 1.15 mmol) was added dropwise. The mixture was heated to 60° C. overnight. After cooling to RT saturated aqueous NH4Cl was added. The mixture was extracted with EtOAc. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (SiO2, EtOAc:hexanes 1:1) to afford 3-{2-[4-(2,6-dichloro-4-ethyl-benzyloxy)-phenyl]-morpholin-4-yl}-propionic acid tert-butyl ester (115.00 mg)

Workup

  1. temperatureThe mixture was heated to 60° C. overnight
  2. additionwas added
  3. extractionThe mixture was extracted with EtOAc
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (SiO2, EtOAc:hexanes 1:1)

Sources & evidence

ORD record
ord-8cc0f77181a64bb08a4093baeeac586e
Source dataset
uspto-grants-2016_03
Patent number
US09273017B2

Reaction notes

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