Tetrabutylammonium Fluoride → HCID 59201346, compound

HRID 451720Notes

Reaction equation

HRID 451720 reaction equation
[Si]([O:8][CH2:9][CH2:10][O:11][C@:12]([C@@H:23]1[CH2:28][CH2:27][CH2:26][N:25]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:24]1)([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=1)[CH2:13][CH2:14][CH3:15])(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>CC#N>[Cl:22][C:18]1[CH:17]=[C:16]([C@@:12]([C@@H:23]2[CH2:28][CH2:27][CH2:26][N:25]([C:29]([O:31][C:32]([CH3:33])([CH3:35])[CH3:34])=[O:30])[CH2:24]2)([O:11][CH2:10][CH2:9][OH:8])[CH2:13][CH2:14][CH3:15])[CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59201612HCID 59201612, compound

Product 1

HCID 59201346HCID 59201346, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of (R)-tert-butyl 3-((R)-1-(2-(tert-butyldimethylsilyloxy)ethoxy)-1-(3-chlorophenyl)butyl)piperidine-1-carboxylate (1.1 g, 2.1 mmol) in MeCN (5 mL), TBAF (1.1 g, 4.2 mmol) was added in portions at rt. The reaction mixture was stirred for 2-3 h at 50-60° C. The solvent was removed in vacuo to the crude product, which was purified by column chromatography to afford (R)-tert-butyl 3-((R)-1-(3-chlorophenyl)-1-(2-hydroxyethoxy)butyl)piperidine-1-carboxylate (750 mg, 87%). 1H NMR (CDCl3, 400 MHz) δ 7.31 (s, 1H), 7.24 (m, 2H), 7.17 (m, 1H), 4.21-3.90 (m, 2H), 3.80 (m, 2H), 3.37 (m, 2H), 2.31 (m, 1H), 2.05 (m, 3H), 1.88 (m, 4H), 1.56 (m, 1H), 1.44 (s, 9H), 1.38-1.10 (m, 2H), 0.95 (t, 3H).

Workup

  1. customThe solvent was removed in vacuo to the crude product, which
  2. customwas purified by column chromatography

Sources & evidence

ORD record
ord-6a02e8982ecd48e6b4adf8ac2191245d
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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