HCID 118207375, compound → HCID 118207447, compound

HRID 1507203Notes

Reaction equation

HRID 1507203 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[CH2:20][CH2:19][N:18]([CH:21]3[CH2:25][CH2:24][N:23]([CH2:26][C:27]4[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=4)[C:22]3=[O:34])[CH2:17][CH:16]2[OH:35])=[CH:11][CH:10]=1)C1C=CC=CC=1.[H][H]>[Pd].CO>[F:33][C:30]1[CH:31]=[CH:32][C:27]([CH2:26][N:23]2[CH2:24][CH2:25][CH:21]([N:18]3[CH2:19][CH2:20][C@H:15]([C:12]4[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=4)[C@H:16]([OH:35])[CH2:17]3)[C:22]2=[O:34])=[CH:28][CH:29]=1

Participants

5

Reactant 2

HCID 118207375HCID 118207375, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 118207447HCID 118207447, compoundYield 101.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3-(4-(4-(benzyloxy)phenyl)-3-hydroxypiperidin-1-yl)-1-(4-fluorobenzyl)-pyrrolidin-2-one (D2 from step E, 85 mg, 0.18 mmol), methanol (5 mL), and 38 mg 10% Pd/C was stirred in a pressure vessel overnight under 125 psi hydrogen pressure. The catalyst was removed by filtration through Celite and the filtrate was evaporated to dryness to yield 70 mg of racemic 1-(4-fluorobenzyl)-3-(cis-3-hydroxy-4-(4-hydroxyphenyl)-piperidin-1-yl)pyrrolidin-2-one. LCMS (method J) RT=0.63 (52% AP), 0.66 (31% AP) min, m/z 385.4 (MH+); 1H NMR (400 MHz, DMSO-d6) δ ppm 7.27-7.28 (m, 2H), 7.15-7.19 (m, 2H), 7.06 (d, J=8.4, 2H), 6.45 (d, J=8.4, 2H), 4.39 (d, J=15, 1H), 4.32 (d, J=15, 1H), 3.74-3.76 (m, 1H), 3.66 (m, 1H), 3.47 (m, 1H), 3.10-3.18 (m, 2H), 3.01 (m, 1H), 2.85-2.88 (m, 1H), 2.76 (m, 1H), 2.30-2.40 (m, 1H), 2.06-2.11 (m, 2H), 1.80-1.95 (m, 1H), 1.46 (d, J=12, 1H). The complete relative stereochemistry was not determined.

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-2fe227c1805a4d01ab87842c6dec9d31
Source dataset
uspto-grants-2015_12
Patent number
US09221796B2

Reaction notes

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