Borane;tetrahydrofuran → HCID 22730070, compound

HRID 2356091Notes

Reaction equation

HRID 2356091 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>>[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

3

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 3538358HCID 3538358, compound

Product 1

HCID 22730070HCID 22730070, compound

Procedure

A solution of Example 266A (0.5 g, 2.82 mmol) in TH 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-0ab081b45d794a5bb5cf7f817fb03c19
Source dataset
uspto-grants-2010_07
Patent number
US07754886B2

Reaction notes

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