3-[(R*)-1-((S)-5-benzyloxy-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-piperidin-3-yl]-phenol → (S)-2-[(R*)-3-(3-Hydroxy-phenyl)-piperidin-1-ylmethyl]-2,3-dihydro-benzo[1,4]dioxin-5-ol

HRID 2366045Notes

Reaction equation

HRID 2366045 reaction equation
C([O:8][C:9]1[C:18]2[O:17][CH2:16][C@H:15]([CH2:19][N:20]3[CH2:25][CH2:24][CH2:23][C@H:22]([C:26]4[CH:27]=[C:28]([OH:32])[CH:29]=[CH:30][CH:31]=4)[CH2:21]3)[O:14][C:13]=2[CH:12]=[CH:11][CH:10]=1)C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[OH:32][C:28]1[CH:27]=[C:26]([C@H:22]2[CH2:23][CH2:24][CH2:25][N:20]([CH2:19][C@@H:15]3[O:14][C:13]4[CH:12]=[CH:11][CH:10]=[C:9]([OH:8])[C:18]=4[O:17][CH2:16]3)[CH2:21]2)[CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 1

HCID 684875373-[(R*)-1-((S)-5-benzyloxy-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-piperidin-3-yl]-phenol

Product 1

HCID 68486843(S)-2-[(R*)-3-(3-Hydroxy-phenyl)-piperidin-1-ylmethyl]-2,3-dihydro-benzo[1,4]dioxin-5-olYield 100.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-[(R*)-1-((S)-5-benzyloxy-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-piperidin-3-yl]-phenol (84 mg, 0.19 mmol) and palladium-on-carbon (60 mg) in ethyl acetate (10 ml) were stirred and hydrogenated for 6 h. The reaction mixture was filtered and washed with ethyl acetate (10 ml), and evaporated to dryness. The crude product was purified with flash chromatography using dichloromethane and methanol as eluents to give 65 mg of the title compound.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with ethyl acetate (10 ml)
  3. customevaporated to dryness
  4. customThe crude product was purified with flash chromatography

Sources & evidence

ORD record
ord-bd933d2dbf4e48fc807b1818beb32da3
Source dataset
uspto-grants-2014_04
Patent number
US08697723B2

Reaction notes

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