Hexane → 1-(1,1-Dimethylethyl) 2-(phenylmethyl) 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-1,2-dicarboxylate

HRID 510958Notes

Reaction equation

HRID 510958 reaction equation
I[C:2]1[CH:3]=[C:4]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH:6]=1.C(O[B:28]1[O:32][C:31]([CH3:34])([CH3:33])[C:30]([CH3:36])([CH3:35])[O:29]1)(C)C.C([Li])CCC.CCCCCC>C1COCC1>[CH3:35][C:30]1([CH3:36])[C:31]([CH3:34])([CH3:33])[O:32][B:28]([C:2]2[CH:3]=[C:4]([C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:15])[N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH:6]=2)[O:29]1

Participants

6

Reactant 4

HCID 8058Hexane2×HCID 50177412-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 59402334HCID 59402334, compoundHCID 178418339Butyllithium2×

Product 1

HCID 594023871-(1,1-Dimethylethyl) 2-(phenylmethyl) 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-1,2-dicarboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At −78° C. to a solution of 2-benzyl 1-tert-butyl 4-iodo-1H-pyrrole-1,2-dicarboxylate (10.0 g, 23.4 mmol), and 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (9.6 mL, 47 mmol) in THF (120 mL) was added dropwise a solution of 2.5 M n-butyllithium in hexane (11.2 mL, 28.1 mmol) with stirring. After completion of addition the mixture was stirred at this temperature for 35 min and then 2.5 M n-butyllithium in hexane (1.87 mL, 4.68 mmol) was added and stirred for another 30 minutes. The reaction was quenched with sat. NH4Cl solution and then diluted with EtOAc. The organic layer was separated, washed with water twice, washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The product was isolated by chromatography eluting with 0 to 10% EtOAc in hexanes. LCMS calculated for C19H23BNO6 (M−[tBu+1]+1)+: m/z=372.2. found: 372.2.

Workup

  1. additionAfter completion of addition the mixture
  2. stirringwas stirred at this temperature for 35 min
  3. stirringstirred for another 30 minutes
  4. customThe reaction was quenched with sat. NH4Cl solution
  5. additiondiluted with EtOAc
  6. customThe organic layer was separated
  7. washwashed with water twice
  8. washwashed with brine
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated under reduced pressure
  11. customThe product was isolated by chromatography
  12. washeluting with 0 to 10% EtOAc in hexanes

Sources & evidence

ORD record
ord-5ab538a936b04015ae30934cf437e127
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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