(3R)-3-{4-[2-(Morpholine-4-sulfonyl)-vinyl]-phenyl}-cyclopentanone → (3R)-3-{4-[2-(Morpholine-4-sulfonyl)-ethyl]-phenyl}-cyclopentanone

HRID 1614871Notes

Reaction equation

HRID 1614871 reaction equation
[N:1]1([S:7]([CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][C:15]([C@@H:18]3[CH2:22][CH2:21][C:20](=[O:23])[CH2:19]3)=[CH:14][CH:13]=2)(=[O:9])=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1>CCOC(C)=O.[Pd]>[N:1]1([S:7]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C@@H:18]3[CH2:22][CH2:21][C:20](=[O:23])[CH2:19]3)=[CH:14][CH:13]=2)(=[O:9])=[O:8])[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 68748916(3R)-3-{4-[2-(Morpholine-4-sulfonyl)-vinyl]-phenyl}-cyclopentanone

Product 1

HCID 68751067(3R)-3-{4-[2-(Morpholine-4-sulfonyl)-ethyl]-phenyl}-cyclopentanone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (3R)-3-{4-[2-(morpholine-4-sulfonyl)-vinyl]-phenyl}-cyclopentanone (210 mg) in EtOAc (10 ml) containing Pd/C (10%, 50 mg) was hydrogenated over night at r.t. The mixture is filtered and solvents are removed in vacuo to afford the 1H NMR (300 MHz, CDCl3) δ 7.25-7.17 (m, 4H), 3.75 (m, 4H), 3.48-3.34 (m, 1H), 3.32-3.23 (m, 4H), 3.21-3.07 (m, 4H), 2.72-2.61 (m, 1H), 2.53-2.22 (m, 4H), 2.01-1.89 (m, 1H).

Workup

  1. waitwas hydrogenated over night at r.t
  2. filtrationThe mixture is filtered
  3. customsolvents are removed in vacuo
  4. customto afford the 1H NMR (300 MHz, CDCl3) δ 7.25-7.17 (m, 4H), 3.75 (m, 4H), 3.48-3.34 (m, 1H), 3.32-3.23 (m, 4H), 3.21-3.07 (m, 4H), 2.72-2.61 (m, 1H), 2.53-2.22 (m, 4H), 2.01-1.89 (m, 1H)

Sources & evidence

ORD record
ord-d7498ff9d58347c9b9a1ac28d4730f2f
Source dataset
uspto-grants-2014_07
Patent number
US08765676B2

Reaction notes

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