HCID 131734370, compound → HCID 118207399, compound

HRID 1507221Notes

Reaction equation

HRID 1507221 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@H:15]2[CH2:20][CH2:19][N:18]([C@@H:21]3[CH2:25][CH2:24][N:23]([CH2:26][C:27]4[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=4)[C:22]3=[O:34])[CH2:17][CH:16]2[F:35])=[CH:11][CH:10]=1)C1C=CC=CC=1>CO>[F:35][C@@H:16]1[C@@H:15]([C:12]2[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=2)[CH2:20][CH2:19][N:18]([CH:21]2[CH2:25][CH2:24][N:23]([CH2:26][C:27]3[CH:28]=[CH:29][C:30]([CH3:33])=[CH:31][CH:32]=3)[C:22]2=[O:34])[CH2:17]1

Participants

3

Reactant 1

HCID 131734370HCID 131734370, compound

Product 1

HCID 118207399HCID 118207399, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-((3R,4R)-(4-(4-(benzyloxy)phenyl)-3-fluoropiperidin-1-yl)-1-(4-methylbenzyl)pyrrolidin-2-one (382 mg, 0.81 mmol) and methanol (4 mL) was flushed with nitrogen, followed by the addition of 172 mg of 10% Pd/C. Then the mixture was stirred at rt overnight under 25-99 psi hydrogen pressure. The reaction was then transferred to a 100 mL autoclave and stirred at 7 kg/cm2 hydrogen pressure for 4 days. The catalyst was removed by filtration through Celite and the solvent was evaporated off. The crude product was subjected to HPLC purification (method B) to yield 77.3 mg 3-((3R,4R)-3-fluoro-4-(4-hydroxyphenyl)-piperidin-1-yl)-1-(4-methylbenzyl)pyrrolidin-2-one (diastereomeric pair) LCMS (method Q) RT 1.15 min, m/z 383.0 (M+H+).

Workup

  1. customwas flushed with nitrogen
  2. additionfollowed by the addition of 172 mg of 10% Pd/C
  3. stirringstirred at 7 kg/cm2 hydrogen pressure for 4 days
  4. customThe catalyst was removed by filtration through Celite
  5. customthe solvent was evaporated off
  6. customThe crude product was subjected to HPLC purification (method B)

Sources & evidence

ORD record
ord-34733723b62d4c62bb9b699ae09fa970
Source dataset
uspto-grants-2015_12
Patent number
US09221796B2

Reaction notes

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