HCID 68430597, compound → HCID 59134307, compound

HRID 2425366Notes

Reaction equation

HRID 2425366 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 68430597HCID 68430597, compound

Product 1

HCID 59134307HCID 59134307, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of (3R*,4R*)-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 sodium carbonate aqueous 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. additionsodium carbonate aqueous 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-075d8f3459cc42a0a7848cf55aebd3cb
Source dataset
uspto-grants-2011_06
Patent number
US07964623B2

Reaction notes

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