Tetrabutylammonium Fluoride → tert-Butyl (3R,4S)-3-({cyclopropyl[3-hydroxy-5-(3-methoxypropyl)benzyl]-amino}carbonyl)-4-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}piperidine-1-carboxylate

HRID 658254Notes

Reaction equation

HRID 658254 reaction equation
[Si]([O:8][C:9]1[CH:10]=[C:11]([CH:51]=[C:52]([CH2:54][CH2:55][CH2:56][O:57][CH3:58])[CH:53]=1)[CH2:12][N:13]([CH:48]1[CH2:50][CH2:49]1)[C:14]([C@@H:16]1[C@@H:21]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][O:31][C:32]3[C:37]([Cl:38])=[CH:36][C:35]([CH3:39])=[CH:34][C:33]=3[Cl:40])=[CH:24][CH:23]=2)[CH2:20][CH2:19][N:18]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:17]1)=[O:15])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH:48]1([N:13]([CH2:12][C:11]2[CH:51]=[C:52]([CH2:54][CH2:55][CH2:56][O:57][CH3:58])[CH:53]=[C:9]([OH:8])[CH:10]=2)[C:14]([C@@H:16]2[C@@H:21]([C:22]3[CH:23]=[CH:24][C:25]([O:28][CH2:29][CH2:30][O:31][C:32]4[C:37]([Cl:38])=[CH:36][C:35]([CH3:39])=[CH:34][C:33]=4[Cl:40])=[CH:26][CH:27]=3)[CH2:20][CH2:19][N:18]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:17]2)=[O:15])[CH2:50][CH2:49]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86639853tert-Butyl (3R,4S)-3-{[[3-{[tert-butyl(dimethyl)silyl]oxy}-5-(3-methoxy-propyl)benzyl](cyclopropyl)amino]carbonyl}-4-{4-[2-(2,6-dichloro-4-methyl-phenoxy)ethoxy]phenyl}piperidine-1-carboxylate

Product 1

HCID 68492454tert-Butyl (3R,4S)-3-({cyclopropyl[3-hydroxy-5-(3-methoxypropyl)benzyl]-amino}carbonyl)-4-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of tert-butyl (3R,4S)-3-{[[3-{[tert-butyl(dimethyl)silyl]oxy}-5-(3-methoxypropyl)benzyl](cyclopropyl)amino]carbonyl}-4-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}piperidine-1-carboxylate (1 eq.) from the previous step in THF (0.1 M) was added a solution of 1 M tetrabutylammonium fluoride in THF (1.3 eq.). The reaction was stirred at it for 1 h and then concentrated in vacuo. The residue was purified by flash column chromatography (SiO2, 50% EtOAc in Hex) to afford the title compound as a foam.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by flash column chromatography (SiO2, 50% EtOAc in Hex)

Sources & evidence

ORD record
ord-96d91b848b3c454ba5754069dd17e40b
Source dataset
uspto-grants-2011_12
Patent number
US08076359B2

Reaction notes

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