1,2,3,4-Tetrahydroisoquinoline → HCID 86729264, compound

HRID 1051484Notes

Reaction equation

HRID 1051484 reaction equation
[O:1]1[CH2:3][CH:2]1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH:9]=[CH:10][CH:11]=1.[CH2:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23][CH2:22][NH:21]1>CCO>[CH2:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23][CH2:22][N:21]1[CH2:3][CH:2]([OH:1])[CH2:4][O:5][C:6]1[CH:7]=[C:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 86729263HCID 86729263, compound

Product 1

HCID 86729264HCID 86729264, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of tert-butyl (3-(oxiran-2-ylmethoxy)phenyl)carbamate 1.5 g, 5.66 mmol) in EtOH (30 mL) was added 1,2,3,4-tetrahydroisoquinoline 0.828 g, 6.23 mmol). The reaction mixture was heated at 100° C. for 4 h. The solvent was then removed by concentration and the residue dissolved in ethyl acetate, washed with water and the separated organic layer dried over sodium sulfate and concentrated to obtain a crude product. This product was used in next step without further purification.

Workup

  1. customThe solvent was then removed by concentration
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washwashed with water
  4. dry with materialthe separated organic layer dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-51fdd328dcbd48eda8ac70703671b3df
Source dataset
uspto-grants-2016_07
Patent number
US09388173B2

Reaction notes

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