tert-butyl 5-(benzyloxy)-6-methoxy-3,4-dihydroisoquinoline-2(1H)-carboxylate → tert-butyl 5-hydroxy-6-methoxy-3,4-dihydroisoquinoline-2(1H)-carboxylate

HRID 717370Notes

Reaction equation

HRID 717370 reaction equation
C([O:8][C:9]1[C:18]([O:19][CH3:20])=[CH:17][CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][N:13]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:14]2)C1C=CC=CC=1>CO.[Pd].C(OCC)(=O)C>[OH:8][C:9]1[C:18]([O:19][CH3:20])=[CH:17][CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][N:13]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:14]2

Participants

5

Reactant 1

HCID 90411333tert-butyl 5-(benzyloxy)-6-methoxy-3,4-dihydroisoquinoline-2(1H)-carboxylate

Product 1

HCID 90411670tert-butyl 5-hydroxy-6-methoxy-3,4-dihydroisoquinoline-2(1H)-carboxylate

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 23938PalladiumSolvent

Procedure

Into a 50-mL 3-necked round-bottom flask, was placed a solution of tert-butyl 5-(benzyloxy)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-2-carboxylate (5.5 g, 14.89 mmol, 1.00 equiv) in MeOH (20 mL) and Pd/C (0.55 g). To the above H2 (enough, gas) was introduced in. The resulting solution was stirred overnight at room temperature. The solids were filtered out. The resulting mixture was concentrated under vacuum. This resulted in 3.6 g (87%) of tert-butyl 5-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline-2-carboxylate as a light yellow solid. MS (ESI) m/z 224 ([M+H-t-butyl]+); Rf: 0.15 (starting material) and 0.32 (product) in ethyl acetate:petroleum ether=1:5.

Workup

  1. customInto a 50-mL 3-necked round-bottom flask, was placed
  2. additionTo the above H2 (enough, gas) was introduced in
  3. filtrationThe solids were filtered out
  4. concentrationThe resulting mixture was concentrated under vacuum
  5. customThis resulted in 3.6 g (87%) of tert-butyl 5-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline-2-carboxylate as a light yellow solid

Sources & evidence

ORD record
ord-7757585eb7944fa38e5b2e6844963023
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

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