HCID 66833546, compound → 3-{2-[(Tert-butoxy)carbonyl]-1,2,3,4-tetrahydroisoquinolin-3-yl}propanoic acid

HRID 579532Notes

Reaction equation

HRID 579532 reaction equation
C([O:3][C:4](=[O:24])/[CH:5]=[CH:6]/[CH:7]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][N:8]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])C>C(O)C.[Pd]>[C:20]([O:19][C:17]([N:8]1[CH:7]([CH2:6][CH2:5][C:4]([OH:24])=[O:3])[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9]1)=[O:18])([CH3:23])([CH3:21])[CH3:22]

Participants

4

Reactant 1

HCID 66833546HCID 66833546, compound

Product 1

HCID 668329413-{2-[(Tert-butoxy)carbonyl]-1,2,3,4-tetrahydroisoquinolin-3-yl}propanoic acidYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of (E)-tert-butyl 3-(3-ethoxy-3-oxoprop-1-enyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (8.7 g, 26.3 mmol) and Pd/C (cat) in ethanol (150 mL, 0.18 M) was evacuated to remove air then treated with hydrogen via a balloon. After stirring for 4 h, 3 M sodium hydroxide was added to adjust the solution to pH 11 and the mixture was stirred overnight. The resulting solution was filtered, concentrated, acidified to pH 2 and extracted with ethyl acetate. The organic layer was dried over MgSO4, filtered and concentrated to give 3-(2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinolin-3-yl)propanoic acid as a yellow oil (7.7 g, 96%). ESI MS found for C17H23NO4 m/z [328.4 (M+23)]. The crude product was used without further purification.

Workup

  1. customto remove air
  2. additionthen treated with hydrogen via a balloon
  3. addition3 M sodium hydroxide was added
  4. stirringthe mixture was stirred overnight
  5. filtrationThe resulting solution was filtered
  6. concentrationconcentrated
  7. extractionextracted with ethyl acetate
  8. dry with materialThe organic layer was dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-e13e7949c8cb4fa0b2fdd75b38582697
Source dataset
uspto-grants-2015_05
Patent number
US09040703B2

Reaction notes

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