3-[4-[2-[4-(Benzyloxy)phenoxy]ethyl]-1-piperidinyl]-5-[[1-(tert-butoxycarbonyl)-2(S)-pyrrolidinyl]methoxy]pyridine → 3-[4-[2-(4-Hydroxyphenoxy)ethyl]-1-piperidinyl]-5-[[1-(tert-butoxycarbonyl)-2(S)-pyrrolidinyl]methoxy]pyridine

HRID 2095441Notes

Reaction equation

HRID 2095441 reaction equation
C([O:8][C:9]1[CH:43]=[CH:42][C:12]([O:13][CH2:14][CH2:15][CH:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:23]=[N:24][CH:25]=[C:26]([O:28][CH2:29][C@@H:30]4[CH2:34][CH2:33][CH2:32][N:31]4[C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH:27]=3)[CH2:18][CH2:17]2)=[CH:11][CH:10]=1)C1C=CC=CC=1>[Pd].CO.C(Cl)Cl>[OH:8][C:9]1[CH:43]=[CH:42][C:12]([O:13][CH2:14][CH2:15][CH:16]2[CH2:17][CH2:18][N:19]([C:22]3[CH:23]=[N:24][CH:25]=[C:26]([O:28][CH2:29][C@@H:30]4[CH2:34][CH2:33][CH2:32][N:31]4[C:35]([O:37][C:38]([CH3:39])([CH3:40])[CH3:41])=[O:36])[CH:27]=3)[CH2:20][CH2:21]2)=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 593716803-[4-[2-[4-(Benzyloxy)phenoxy]ethyl]-1-piperidinyl]-5-[[1-(tert-butoxycarbonyl)-2(S)-pyrrolidinyl]methoxy]pyridine

Product 1

HCID 593715663-[4-[2-(4-Hydroxyphenoxy)ethyl]-1-piperidinyl]-5-[[1-(tert-butoxycarbonyl)-2(S)-pyrrolidinyl]methoxy]pyridineYield 102.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21226129Dichloromethane methanolSolvent

Procedure

A mixture of 3-[4-[2-[4-(benzyloxy)phenoxy]ethyl]-1-piperidinyl]-5-[[1-(tert-butoxycarbonyl)-2(S)-pyrrolidinyl]methoxy]pyridine (300 mg, 0.51 mmol) and palladium on carbon (60 mg) in MeOH/CH2Cl2 (20/7 mL) was stirred at room temperature overnight under H2. TLC analysis of the reaction mixture indicated that the starting material had disappeared. The solids were filtered off, and the filtrate was concentrated under vacuum to provide the title compound (260 mg, 92%) as a yellow solid. 1H NMR (DMSO-d6, 300 MHz) δ 8.88 (s, 1H), 7.91 (s, 1H), 7.70 (s, 1H), 6.97 (s, 1H), 6.75 (d, 2H, J=8.7 Hz), 6.66 (d, 2H, J=9.0 Hz), 4.05-4.01 (m, 3H), 3.92-3.90 (m, 2H), 3.77 (m, 2H), 3.32 (m, 2H), 2.74-2.71 (m, 2H), 1.99-1.65 (m, 7H), 1.40 (s, 9H), 1.38-1.18 (m, 4H). LC-MS (ESI) m/z 498 (M+H+).

Workup

  1. filtrationThe solids were filtered off
  2. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-5215a58c355d4ead9bda39461340cb46
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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