5-[(1R)-2-{4-[2-(1,1-dioxido-1-benzothiophen-5-yl)-2-oxoethyl]piperazin-1-yl}-1-hydroxyethyl]-4-methyl-2-benzofuran-1 (3H)-one → 5-[(1R)-2-{4-[2-(1,1-dioxido-2,3-dihydro-1-benzothiophen-5-yl)-2-oxoethyl]piperazin-1-yl}-1-hydroxyethyl]-4-methyl-2-benzofuran-1(3H)-one

HRID 2281358Notes

Reaction equation

HRID 2281358 reaction equation
[O:1]=[S:2]1(=[O:34])[C:6]2[CH:7]=[CH:8][C:9]([C:11](=[O:33])[CH2:12][N:13]3[CH2:18][CH2:17][N:16]([CH2:19][C@@H:20]([C:22]4[CH:31]=[CH:30][C:25]5[C:26](=[O:29])[O:27][CH2:28][C:24]=5[C:23]=4[CH3:32])[OH:21])[CH2:15][CH2:14]3)=[CH:10][C:5]=2[CH:4]=[CH:3]1>C(Cl)Cl.[Pd]>[O:34]=[S:2]1(=[O:1])[C:6]2[CH:7]=[CH:8][C:9]([C:11](=[O:33])[CH2:12][N:13]3[CH2:14][CH2:15][N:16]([CH2:19][C@@H:20]([C:22]4[CH:31]=[CH:30][C:25]5[C:26](=[O:29])[O:27][CH2:28][C:24]=5[C:23]=4[CH3:32])[OH:21])[CH2:17][CH2:18]3)=[CH:10][C:5]=2[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 1176419265-[(1R)-2-{4-[2-(1,1-dioxido-1-benzothiophen-5-yl)-2-oxoethyl]piperazin-1-yl}-1-hydroxyethyl]-4-methyl-2-benzofuran-1 (3H)-one

Product 1

HCID 1176421725-[(1R)-2-{4-[2-(1,1-dioxido-2,3-dihydro-1-benzothiophen-5-yl)-2-oxoethyl]piperazin-1-yl}-1-hydroxyethyl]-4-methyl-2-benzofuran-1(3H)-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 5-[(1R)-2-{4-[2-(1,1-dioxido-1-benzothiophen-5-yl)-2-oxoethyl]piperazin-1-yl}-1-hydroxyethyl]-4-methyl-2-benzofuran-1(3H)-one (56 mg, 0.12 mmol) in DCM (5 mL) was added to a slurry of 10% Pd/C (3.7 mg, 0.30 mmol) in DCM (5 mL). This solution was then subjected to hydrogenation conditions (1 atm @23° C. for 15 hours) and then filtered over a pad of Celite® diatomaceous earth and concentrated in vacuo to afford 5-[(1R)-2-{4-[2-(1,1-dioxido-2,3-dihydro-1-benzothiophen-5-yl)-2-oxoethyl]piperazin-1-yl}-1-hydroxyethyl]-4-methyl-2-benzofuran-1(3H)-one which was used without further purification.

Workup

  1. customwas then subjected to hydrogenation conditions (1 atm @23° C. for 15 hours)
  2. filtrationfiltered over a pad of Celite® diatomaceous earth
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c654baec0a414cce8537a252759c3ad3
Source dataset
uspto-grants-2015_09
Patent number
US09139585B2

Reaction notes

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