Boron tribromide → HCID 57725575, compound

HRID 2370544Notes

Reaction equation

HRID 2370544 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 vaccuo, 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 vaccuo
  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-5b1e5ccd970a44ac90438c4d7bce07e2
Source dataset
uspto-grants-2014_04
Patent number
US08710048B2

Reaction notes

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