HCID 67245490, compound → HCID 59134307, compound

HRID 1993491Notes

Reaction equation

HRID 1993491 reaction equation
[OH:1][C@H:2]1[C:18]([CH3:20])([CH3:19])[O:17][C:5]2=[CH:6][C:7]3[C:8]([CH3:16])=[CH:9][C:10]([C:14]#[N:15])=[N:11][C:12]=3[CH:13]=[C:4]2[C@@H:3]1[NH:21][CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(O)(=O)C.[Pd]>[NH2:15][CH2:14][C:10]1[CH:9]=[C:8]([CH3:16])[C:7]2[CH:6]=[C:5]3[O:17][C:18]([CH3:20])([CH3:19])[C@H:2]([OH:1])[C@@H:3]([NH:21][CH2:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C:4]3=[CH:13][C:12]=2[N:11]=1

Participants

4

Reactant 1

HCID 67245490HCID 67245490, compound

Product 1

HCID 59134307HCID 59134307, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of (3R*,4S*)-3-hydroxy-2,2,9-trimethyl-4-[(2-phenylethyl)amino]-3,4-dihydro-2H-pyrano[2,3-g]quinoline-7-carbonitrile described in Synthesis Example 14(110 mg, 0.283 mmol) in acetic acid (5 mL), 10% Pd/C (22 mg) was added at room temperature, and the resulting mixture was stirred for 2 hours under hydrogen atmosphere. Upon the completion of the reaction, the resulting solution was filtered through celite, the solvent was distilled off and then aqueous sodium carbonate solution was added to the residue, and the resulting solution was extracted with chloroform, dried over anhydrous magnesium sulfate, and the solvent was distilled off to obtain crude product of (3R*,4S*)-7-aminomethyl-2,2,9-trimethyl-4-[(2-phenylethyl)amino]-3,4-dihydro-2H-pyrano[2,3-g]quinolin-3-ol (75.1 mg).

Workup

  1. additionwas added at room temperature
  2. customUpon the completion of the reaction
  3. filtrationthe resulting solution was filtered through celite
  4. distillationthe solvent was distilled off
  5. additionaqueous sodium carbonate solution was added to the residue
  6. extractionthe resulting solution was extracted with chloroform
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-d63d7ee87e534164af07e544ae698035
Source dataset
uspto-grants-2010_01
Patent number
US07652008B2

Reaction notes

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