tert-Butyl 6-nitro-3,4-dihydroisoquinoline-2(1H)-carboxylate → 6-Amino-2-N-Boc-1,2,3,4-tetrahydro-isoquinoline

HRID 1954422Notes

Reaction equation

HRID 1954422 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([N+:18]([O-])=O)[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1COCC1.[Pt]>[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([NH2:18])[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 15491253tert-Butyl 6-nitro-3,4-dihydroisoquinoline-2(1H)-carboxylate

Product 1

HCID 27563716-Amino-2-N-Boc-1,2,3,4-tetrahydro-isoquinolineYield 58.3%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The 6-nitro-3,4-dihydro-1H-isoquinoline2-carboxylic acid tert-butyl ester (82 mg, 0.29 mmol) in THF (2 mL) was hydrogenated with 5% Pt-C (50% water wet, 10 mg) at 50 psi for 5 hrs. The catalyst was filtered off, the solvent was removed under vacuum and the residue chromatographed on silica with ethyl acetate/hexanes to give 42 mg (57%) of the title product.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent was removed under vacuum
  3. customthe residue chromatographed on silica with ethyl acetate/hexanes

Sources & evidence

ORD record
ord-35f5375c51874de9a07cfa762abc5693
Source dataset
uspto-grants-2000_09
Patent number
US06121283

Reaction notes

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