HCID 68281390, compound → HCID 68281431, compound

HRID 1425938Notes

Reaction equation

HRID 1425938 reaction equation
CC1(C)C(C)(C)[O:5][B:4]([C:9]2[CH:18]=[C:17]3[C:12]([CH2:13][CH2:14][NH:15][CH2:16]3)=[CH:11][CH:10]=2)[O:3]1>Cl>[CH2:16]1[C:17]2[C:12](=[CH:11][CH:10]=[C:9]([B:4]([OH:5])[OH:3])[CH:18]=2)[CH2:13][CH2:14][NH:15]1

Participants

3

Reactant 1

HCID 68281390HCID 68281390, compound

Product 1

HCID 68281431HCID 68281431, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

7-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydroisoquinoline (CXXI) (0.3 g, 1.15 mmol) was dissolved in 6 N aqueous HCl (20 mL) and refluxed overnight. The solvent was evaporated to dryness and the residue was crystallized from MeOH/Et2O to give 1,2,3,4-tetrahydroisoquinolin-7-ylboronic acid (CXXII) as a brown solid (0.21 g, 0.98 mmol, 87% yield). 1H NMR (DMSO-d6) δ ppm 2.92-3.07 (m, 2H), 3.36 (brs, 2H), 4.22 (brs, 2H), 7.18 (d, J=7.56 Hz, 1H), 7.59 (s, 1H), 7.67 (d, J=6.87 Hz, 1H), 8.08 (brs, 1H), 9.66 (brs, 2H); ESIMS found for C9H12BNO2 m/z 178 (M+H).

Workup

  1. temperaturerefluxed overnight
  2. customThe solvent was evaporated to dryness
  3. customthe residue was crystallized from MeOH/Et2O

Sources & evidence

ORD record
ord-5f4e80e26b8c423585f95a66b1b582fa
Source dataset
uspto-grants-2015_01
Patent number
US08933018B2

Reaction notes

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