Methoxy-phenyl-acetic acid {1-[2-(4-fluoro-phenyl)-ethyl]-piperidin-4-yl}-(2-methoxy-3-triisopropylsilanyloxy-phenyl)-methyl ester → (S)-Methoxy-2-phenyl-acetic acid {1-[2-(4-fluoro-phenyl)-ethyl]-piperidin-4-yl}-(3-hydroxy-2-methoxy-phenyl)-methyl ester

HRID 991563Notes

Reaction equation

HRID 991563 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([CH:16]([O:36][C:37](=[O:47])[CH:38]([O:45][CH3:46])[C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][Si](C(C)C)(C(C)C)C(C)C)[C:18]=3[O:34][CH3:35])[CH2:12][CH2:11]2)=[CH:4][CH:3]=1.[F-].[F-].[F-].[F-].[NH4+].[NH4+].[NH4+].[NH4+]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([CH:16]([O:36][C:37](=[O:47])[C@@H:38]([O:45][CH3:46])[C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)[C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([OH:23])[C:18]=3[O:34][CH3:35])[CH2:12][CH2:11]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 21305588Methoxy-phenyl-acetic acid {1-[2-(4-fluoro-phenyl)-ethyl]-piperidin-4-yl}-(2-methoxy-3-triisopropylsilanyloxy-phenyl)-methyl esterHCID 22393694Ammonium tetrafluoride

Product 1

HCID 60077790(S)-Methoxy-2-phenyl-acetic acid {1-[2-(4-fluoro-phenyl)-ethyl]-piperidin-4-yl}-(3-hydroxy-2-methoxy-phenyl)-methyl ester

Procedure

Add to methoxy-phenyl-acetic acid {1-[2-(4-fluoro-phenyl)-ethyl]-piperidin-4-yl}-(2-methoxy-3-triisopropylsilanyloxy-phenyl)-methyl ester, Example 1C (207 g, 0.3111 mol) a 0.5M solution of methanolic ammonium tetrafluoride (1.2 L, 0.6 mol) and reflux for 17.5 h. Concentrate and obtain 198 g of the title compound.

Workup

  1. temperaturereflux for 17.5 h
  2. concentrationConcentrate

Sources & evidence

ORD record
ord-4e0ac294a9e1446b9ed32bc3d204b920
Source dataset
uspto-grants-2002_10
Patent number
US06465490B1

Reaction notes

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