Borane;tetrahydrofuran → HCID 22730070, compound

HRID 1785818Notes

Reaction equation

HRID 1785818 reaction equation
[CH3:1][C:2]([S:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([CH3:5])[C:3]#[N:4].B.C1COCC1>C1COCC1>[CH3:5][C:2]([S:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([CH3:1])[CH2:3][NH2:4]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 3538358HCID 3538358, compound

Product 1

HCID 22730070HCID 22730070, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of Example 266A (0.5 g, 2.82 mmol) in THF at room temperature was treated with 1M BH3.THF (15 mL), stirred for 18 hours, quenched with methanol (5 mL), and concentrated. The concentrate was treated with 2M HCl (50 mL) and concentrated. The the organic phase was dried (MgSO4), filtered, and concentrated to provide the desired product. MS (DCI(+)) m/e 182 (M+H)+.

Workup

  1. customquenched with methanol (5 mL)
  2. concentrationconcentrated
  3. additionThe concentrate was treated with 2M HCl (50 mL)
  4. concentrationconcentrated
  5. dry with materialThe the organic phase was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c007e85484ad4418942dfc3117e45dd2
Source dataset
uspto-grants-2009_03
Patent number
US07504512B2

Reaction notes

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