Boron tribromide → HCID 57725575, compound

HRID 1988454Notes

Reaction equation

HRID 1988454 reaction equation
C[O:2][C:3]1[CH:19]=[CH:18][C:6]2[N:7]=[C:8]([NH:10][C@@H:11]3[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]3[OH:17])[S:9][C:5]=2[CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:17][C@@H:12]1[CH2:13][CH2:14][CH2:15][CH2:16][C@H:11]1[NH:10][C:8]1[S:9][C:5]2[CH:4]=[C:3]([OH:2])[CH:19]=[CH:18][C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 57725706HCID 57725706, compound

Product 1

HCID 57725575HCID 57725575, compoundYield 115.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To the solution of (1R,2R)-2-(6-methoxybenzo[d]thiazol-2-ylamino)cyclohexanol (1.06 g, 3.81 mmol) in 16 ml of DCM was added 1 M boron tribromide in DCM (8 ml, 8 mmol) slowly at 0° C. The reaction solution was stirred at room temperature for 2 hours. Removal of all solvent in vacuo, followed by quenching with water (ca. 30 ml) and diluted NaHCO3 solution, and extraction of aqueous phase with ethyl acetate (3×100 ml) and drying of combined organic extracts over Na2SO4 and subsequent removal of ethyl acetate in vaccuo yielded the desired product (1.16 g) as pink solid. The residue was purified by flash column chromatography to give 2-((1R,2R)-2-hydroxycyclohexylamino)benzo[d]thiazol-6-ol (1.0 g, 3.78 mmol) as brown solid. ES/MS m/z 265.1 (MH+).

Workup

  1. customRemoval of all solvent in vacuo
  2. customby quenching with water (ca. 30 ml) and diluted NaHCO3 solution, and extraction of aqueous phase with ethyl acetate (3×100 ml)
  3. dry with materialdrying of combined organic extracts over Na2SO4 and subsequent removal of ethyl acetate in vaccuo

Sources & evidence

ORD record
ord-3b35e360ecfc4d8b898437f0121b9d86
Source dataset
uspto-grants-2009_06
Patent number
US07553854B2

Reaction notes

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