Tetrahydrofuran → HCID 178472380, compound

HRID 2095649Notes

Reaction equation

HRID 2095649 reaction equation
I[C:2]1[C:3]([CH3:18])=[N:4][N:5]([C@H:7]2[CH2:12][CH2:11][C@H:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:9][CH2:8]2)[CH:6]=1.C1COCC1.C([Mg]Cl)(C)C.CO[B:31]1[O:35][C:34]([CH3:37])([CH3:36])[C:33]([CH3:39])([CH3:38])[O:32]1>>[CH3:18][C:3]1[C:2]([B:31]2[O:35][C:34]([CH3:37])([CH3:36])[C:33]([CH3:39])([CH3:38])[O:32]2)=[CH:6][N:5]([C@H:7]2[CH2:12][CH2:11][C@H:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:9][CH2:8]2)[N:4]=1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 109757592-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 178418918HCID 178418918, compoundHCID 178472388HCID 178472388, compound

Product 1

HCID 178472380HCID 178472380, compound

Procedure

To a solution of ethyl trans-4-(4-iodo-3-methyl-1H-pyrazol-1-yl)cyclohexanecarboxylate (120.0 mg, 0.3313 mmol) in THF (6 mL, 80 mmol) was added 2 M isopropylmagnesium chloride in THF (0.66 mL, 1.3 mmol) at rt, and the mixture was stirred for 30 min. 2-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.27 mL, 1.7 mmol) was added, and the mixture stirred at rt for 2 h. The reaction was quenched with sat. NH4Cl, and the organic solvent was removed in vacuo. The material was extracted with DCM and water, and the organic layer was concentrated in vacuo to afford the title compound as a clear oil.

Workup

  1. stirringthe mixture stirred at rt for 2 h
  2. customThe reaction was quenched with sat. NH4Cl
  3. customthe organic solvent was removed in vacuo
  4. extractionThe material was extracted with DCM and water
  5. concentrationthe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-2e0ff93d4d514d49bdb56d5ac4e4877f
Source dataset
uspto-grants-2013_05
Patent number
US08445510B2

Reaction notes

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