Sodium Hydroxide → 2-(t-Butyloxycarbonyl)-7-methoxy-1,2,3,4-tetrahydroisoquinoline-3(S)-carboxylic acid

HRID 1584275Notes

Reaction equation

HRID 1584275 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:17]([C:18]([O:20]C)=[O:19])[CH2:16][C:15]2[C:10](=[CH:11][C:12]([O:22][CH3:23])=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO.O>[C:1]([O:5][C:6]([N:8]1[C@H:17]([C:18]([OH:20])=[O:19])[CH2:16][C:15]2[C:10](=[CH:11][C:12]([O:22][CH3:23])=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21311307Methyl 2-(t-butyloxycarbonyl)-7-methoxy-1,2,3,4-tetrahydroisoquinoline-3(S)-carboxylate

Product 1

HCID 213113022-(t-Butyloxycarbonyl)-7-methoxy-1,2,3,4-tetrahydroisoquinoline-3(S)-carboxylic acid

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
25 °C

Procedure

To a solution of Methyl 2-(t-butyloxycarbonyl)-7-methoxy-1,2,3,4-tetrahydroisoquinoline-3(S)-carboxylate (0.58 g, 1.81 mmol) in MeOH:H2O 1:1 (20 mL) was added 1 N NaOH (2.7 mL, 2.72 mmol) and the resulting solution was stirred at 25° C. for 18 hr. The methanol was evaporated in vacuo and the remaining aqueous portion was acidified to pH=3 with 1 N HCl and then extracted two times with EtOAc. The organic layers were washed with saturated NaCl (30 mL) and dried (MgSO4). Filtration and evaporation in vacuo gave the title compound.

Workup

  1. customThe methanol was evaporated in vacuo
  2. extractionextracted two times with EtOAc
  3. washThe organic layers were washed with saturated NaCl (30 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationFiltration and evaporation in vacuo

Sources & evidence

ORD record
ord-89dce3a3c0bc4bee9f293efebd5e858e
Source dataset
uspto-grants-1999_08
Patent number
US05932590

Reaction notes

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