Diethyl Ether → (S)-2-[(R*)-3-(3-Hydroxy-phenyl)-piperidin-1-ylmethyl]-2,3-dihydro-benzo[1,4]dioxin-6-ol

HRID 2407262Notes

Reaction equation

HRID 2407262 reaction equation
C([O:8][C:9]1[CH:32]=[CH:31][C:12]2[O:13][C@@H:14]([CH2:17][N:18]3[CH2:23][CH2:22][CH2:21][C@H:20]([C:24]4[CH:25]=[C:26]([OH:30])[CH:27]=[CH:28][CH:29]=4)[CH2:19]3)[CH2:15][O:16][C:11]=2[CH:10]=1)C1C=CC=CC=1.C(OCC)C>CCOC(C)=O.[Pd]>[OH:30][C:26]1[CH:25]=[C:24]([C@H:20]2[CH2:21][CH2:22][CH2:23][N:18]([CH2:17][C@@H:14]3[O:13][C:12]4[CH:31]=[CH:32][C:9]([OH:8])=[CH:10][C:11]=4[O:16][CH2:15]3)[CH2:19]2)[CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 251751693-[(R*)-1-((S)-6-Benzyloxy-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-piperidin-3-yl]-phenol

Product 1

HCID 25175171(S)-2-[(R*)-3-(3-Hydroxy-phenyl)-piperidin-1-ylmethyl]-2,3-dihydro-benzo[1,4]dioxin-6-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 10% Pd/C (33 mg) in EtOAc (10 ml) was added 3-[(R*)-1-((S)-6-benzyloxy-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-piperidin-3-yl]-phenol (66 mg, 0.125 mmol). The mixture was stirred under hydrogen for 3 h at normal pressure. The mixture was then filtered and evaporated to give an oil. After trituration with diethyl ether the title compound was obtained as a white solid (40 mg).

Workup

  1. filtrationThe mixture was then filtered
  2. customevaporated
  3. customto give an oil

Sources & evidence

ORD record
ord-10d987836e584acaa5ae32698e482c00
Source dataset
uspto-grants-2014_08
Patent number
US08809536B2

Reaction notes

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