Sodium Carbonate → tert-Butyl 7-bromo-3,4-dihydroisoquinoline-2(1H)-carboxylate

HRID 1477227Notes

Reaction equation

HRID 1477227 reaction equation
Cl.[Br:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][NH:9][CH2:10]2)=[CH:5][CH:4]=1.[C:13]([O-:16])([O-])=[O:14].[Na+].[Na+]>C(Cl)Cl.O>[C:6]([O:16][C:13]([N:9]1[CH2:8][CH2:7][C:6]2[C:11](=[CH:12][C:3]([Br:2])=[CH:4][CH:5]=2)[CH2:10]1)=[O:14])([CH3:11])([CH3:7])[CH3:5]

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 450739697-Bromo-1,2,3,4-tetrahydroisoquinoline--hydrogen chloride (1/1)

Product 1

HCID 15885175tert-Butyl 7-bromo-3,4-dihydroisoquinoline-2(1H)-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 7-bromo-1,2,3,4-tetrahydro-isoquinoline hydrochloride (1.0 g, 4.0 mmol) in DCM (18 mL) and 2M aqueous Na2CO3 solution (5.0 mL, 10.0 mmol) was added a solution of BOC-anhydride (1.0 g, 4.6 mmol) in DCM (7 mL). The reaction mixture was stirred at RT for 3 h and then diluted with water and DCM (1:1, 100 mL). The organic phase was then separated and washed with brine, dried (MgSO4) and filtered. The solvent was evaporated and then carried to next step without purification.

Workup

  1. customThe organic phase was then separated
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customThe solvent was evaporated
  6. customcarried to next step without purification

Sources & evidence

ORD record
ord-474056e00dc7469d818256e13b6d4017
Source dataset
uspto-grants-2016_08
Patent number
US09403782B2

Reaction notes

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