Borane;tetrahydrofuran → HCID 22730070, compound

HRID 2085758Notes

Reaction equation

HRID 2085758 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 concentrate was partitioned between dichloromethane and saturated sodium bicarbonate, and 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. customThe concentrate was partitioned between dichloromethane and saturated sodium bicarbonate
  6. dry with materialthe organic phase was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-3153c364de1745d0a3bb080f29bb9bc6
Source dataset
uspto-grants-2004_04
Patent number
US06720338B2

Reaction notes

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