Hydrochloric Acid → Methyl (1,2,3,4-tetrahydroisoquinolin-1-yl)acetate

HRID 1376053Notes

Reaction equation

HRID 1376053 reaction equation
C([C:8]1([CH2:18][C:19]([OH:21])=[O:20])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10][NH:9]1)(OC(C)(C)C)=O.Cl.[CH3:23]O>>[CH3:23][O:21][C:19](=[O:20])[CH2:18][CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10][NH:9]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887Methanol2×HCID 69227555HCID 69227555, compound

Product 1

HCID 45588337Methyl (1,2,3,4-tetrahydroisoquinolin-1-yl)acetateYield 100%

Procedure

To Boc-tetrahydoisoquinoline-1-acetic acid (100.4 g, 520.0 mmol), in MeOH (200 mL), was added 400 mL of 2.3 M HCl in methanol. The mixture was stirred overnight and then concentrated to dryness. The resulting residue was dissolved in EtOAc, washed with saturated sodium bicarbonate, brine, dried (Na2SO4), and concentrated to dryness; affording 109.5 g (100%) of the ester.

Workup

  1. concentrationconcentrated to dryness
  2. dissolutionThe resulting residue was dissolved in EtOAc
  3. washwashed with saturated sodium bicarbonate, brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-3db5886871594ed3922b0a34ce8f318b
Source dataset
uspto-grants-2007_01
Patent number
US07169777B2

Reaction notes

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