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

HRID 1371523Notes

Reaction equation

HRID 1371523 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) is added 400 mL of 2.3 M HCl in methanol. The mixture is stirred overnight and then concentrated to dryness. The resulting residue is dissolved in EtOAc and washed with saturated sodium bicarbonate and brine, which is then dried (Na2SO4) and concentrated to dryness to afford about 109.5 g (100%) of the ester. EIS-MS 206 [M+1]

Workup

  1. concentrationconcentrated to dryness
  2. dissolutionThe resulting residue is dissolved in EtOAc
  3. washwashed with saturated sodium bicarbonate and brine, which
  4. dry with materialis then dried (Na2SO4)
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-52220eb75c694e6caef4a7305da85b7f
Source dataset
uspto-grants-2007_01
Patent number
US07157463B2

Reaction notes

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