Boron tribromide → HCID 57725575, compound

HRID 2067182Notes

Reaction equation

HRID 2067182 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 a 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. After removal of all solvent in vacuo, the mixture was quenched with water (30 mL) and diluted NaHCO3 solution, and extraction with EtOAc (3×100 mL). The combined organic extracts were dried over Na2SO4 and subsequent removal of EtOAc in vacuo yielded the desired product (1.16 g) as a pink solid. The residue was purified by flash column chromatography to give the title compound (1.0 g, 3.78 mmol) as a brown solid. ES/MS m/z 265.1 (H+).

Workup

  1. customAfter removal of all solvent in vacuo
  2. customthe mixture was quenched with water (30 mL) and diluted NaHCO3 solution, and extraction with EtOAc (3×100 mL)
  3. dry with materialThe combined organic extracts were dried over Na2SO4 and subsequent removal of EtOAc in vacuo

Sources & evidence

ORD record
ord-bf12270d669745e2aad08e4d56e03d61
Source dataset
uspto-grants-2012_10
Patent number
US08293769B2

Reaction notes

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