Boron tribromide → HCID 178467441, compound

HRID 928106Notes

Reaction equation

HRID 928106 reaction equation
[OH:1][C:2]([C@H:9]1[CH2:14][CH2:13][C@H:12]([NH:15]C(=O)OCC2C=CC=CC=2)[CH2:11][CH2:10]1)([C:4]1[S:5][CH:6]=[CH:7][N:8]=1)[CH3:3].B(Br)(Br)Br>ClCCl.CO>[NH2:15][C@H:12]1[CH2:13][CH2:14][C@H:9]([C:2]([C:4]2[S:5][CH:6]=[CH:7][N:8]=2)([OH:1])[CH3:3])[CH2:10][CH2:11]1

Participants

5

Reactant 2

HCID 25134Boron tribromide2×HCID 178467442HCID 178467442, compound

Product 1

HCID 178467441HCID 178467441, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of benzyl {trans-4-[1-hydroxy-1-(1,3-thiazol-2-yl)ethyl]cyclohexyl}-carbamate (895 mg, 2.48 mmol) in dichlormethane at −78° C. was added boron tribromide (1.0 M in dichloromethane, 2.7 mL, 2.7 mmol) dropwise. After one hour, the solution was warmed to 0° C. Another portion of boron tribromide (1.0 M in dichloromethane, 2.7 mL, 2.7 mmol) was then added dropwise and the reaction was allowed to warm to room temperature. The solution was then carefully diluted with methanol and concentrated in vacuo. The residue was purified by chromatography on silica gel to afford 1-(trans-4-aminocyclohexyl)-1-(1,3-thiazol-2-yl)ethanol. MS ESI calc'd. for C11H19N2OS [M+H]+ 227. found 227. 1H NMR (500 MHz, DMSO-d6) δ 7.67 (d, J=3.3, 1H), 7.51 (d, J=3.2, 1H), 5.69 (s, 1H), 2.46-2.39 (m, 1H), 1.80-1.65 (m, 3H), 1.63-1.50 (m, 1H), 1.43 (s, 3H), 1.40-1.32 (m, 1H), 1.24-1.11 (m, 1H), 1.03-0.86 (m, 3H).

Workup

  1. temperatureto warm to room temperature
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-60247f3bba2d4e7eb2a134bb9153140a
Source dataset
uspto-grants-2016_03
Patent number
US09290490B2

Reaction notes

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