Ammonium Chloride → Tert-butyl 6-acetyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate

HRID 564096Notes

Reaction equation

HRID 564096 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:18](=[O:23])N(OC)C)[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:24][Mg]Br.[Cl-].[NH4+]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:18](=[O:23])[CH3:24])[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 18680124HCID 18680124, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 59190846Tert-butyl 6-acetyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-5 °C

Procedure

To 2.30 g (7.18 mmol) 6-(methoxy-methyl-carbamoyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (preparation 29a) in 50 mL THF is added under an argon atmosphere at 0° C. 7.18 mL (21.5 mmol; 3 M solution in diethylether) methylmagnesium bromide. The reaction mixture is stirred 1.5 h at −5° C. and is then transferred into a saturated aqueous ammonium chloride solution. The aqueous phase is extracted three times with tert-butylmethylether, dried over MgSO4, filtered and the solvent is evaporated. The residue is purified by silica gel column chromatography with PE/EtOAc (8:2) as eluent.

Workup

  1. extractionThe aqueous phase is extracted three times with tert-butylmethylether
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customthe solvent is evaporated
  5. customThe residue is purified by silica gel column chromatography with PE/EtOAc (8:2) as eluent

Sources & evidence

ORD record
ord-67a495efb7e649c4be0e2e106d446d9b
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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