Sodium Hydroxide → 6-Bromo-2-pyrrolidin-1-ylmethyl-1,2,3,4-tetrahydro-quinoline

HRID 1916630Notes

Reaction equation

HRID 1916630 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH2:12][N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)[CH:6]=[CH:5]2.[OH-].[Na+]>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]([CH2:12][N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)[CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 673647966-Bromo-2-pyrrolidin-1-ylmethyl-quinoline

Product 1

HCID 673633166-Bromo-2-pyrrolidin-1-ylmethyl-1,2,3,4-tetrahydro-quinoline

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Under an argon atmosphere 0.69 mL (6.87 mmol) borane-pyridine complex are added to a solution of 500 mg (1.72 mmol) 6-bromo-2-pyrrolidin-1-ylmethyl-quinoline (see 3.45b) in 10 mL acetic acid at RT. The mixture is stirred for 7 h at RT, again combined with 0.35 mL (3.46 mmol) borane-pyridine complex and stirred for another hour at RT. It is cooled to 0° C. and the solution is made basic with 8% NaOH solution. The aqueous phase is extracted with EtOAc and the solvent is eliminated i.vac. The residue is taken up with water and acidified with 12% HCl. The aqueous phase is extracted with EtOAc and then made basic with 20% NaOH solution while cooling with ice. The aqueous phase is extracted with EtOAc. The organic phase is dried over MgSO4 and the solvent is eliminated i.vac.

Workup

  1. stirringstirred for another hour at RT
  2. temperatureIt is cooled to 0° C.
  3. extractionThe aqueous phase is extracted with EtOAc
  4. extractionThe aqueous phase is extracted with EtOAc
  5. temperaturewhile cooling with ice
  6. extractionThe aqueous phase is extracted with EtOAc
  7. dry with materialThe organic phase is dried over MgSO4

Sources & evidence

ORD record
ord-e55d78a83c084218aa02717ed7bdf9d0
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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