Boron tribromide → HCID 15657723, compound

HRID 1197554Notes

Reaction equation

HRID 1197554 reaction equation
Cl.C[O:3][C:4]1[CH:5]=[C:6]2[C:15](=[CH:16][CH:17]=1)[CH2:14][CH2:13][C@H:12]1[C@:7]2([NH2:18])[CH2:8][CH:9]=[CH:10][CH2:11]1.B(Br)(Br)Br>C(Cl)Cl>[NH2:18][C@@:7]12[CH2:8][CH:9]=[CH:10][CH2:11][C@@H:12]1[CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][C:4]([OH:3])=[CH:5][C:6]2=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 86745277HCID 86745277, compound

Product 1

HCID 15657723HCID 15657723, compoundYield 55.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of the product from Example 128 (0.20 g) in CH2Cl2 (10 ml) was added BBr3 (2 ml of a 1.0M solution in CH2Cl2. The reaction was stirred at room temperature for 18 hours and quenched by the addition of water. Additional CH2Cl2 (10 ml) and 1N HCl (20 ml) was added. The aqueous phase was separated, and made basic (pH=10) by the addition of NaHCO3. The aqueous phase was extracted with EtOAc (5×10 ml). The combined organic phases were dried over MgSO4, filtered and concentrated. The residue was dissolved in 0.5N HCl and freeze dried to give the title compound as a white solid (90 mg, 41%), mp 156°-161° C.

Workup

  1. customquenched by the addition of water
  2. additionAdditional CH2Cl2 (10 ml) and 1N HCl (20 ml) was added
  3. customThe aqueous phase was separated
  4. additionby the addition of NaHCO3
  5. extractionThe aqueous phase was extracted with EtOAc (5×10 ml)
  6. dry with materialThe combined organic phases were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. dissolutionThe residue was dissolved in 0.5N HCl
  10. customfreeze dried

Sources & evidence

ORD record
ord-be1e5a42f9f44dac9dac5145fc99d30f
Source dataset
uspto-grants-1994_01
Patent number
US05276053

Reaction notes

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