Potassium Carbonate → Tert-butyl 4-[2-(3-ethynylphenyl)-2-(1-hydroxycyclohexyl)ethyl]piperazine-1-carboxylate

HRID 1987005Notes

Reaction equation

HRID 1987005 reaction equation
[OH:1][C:2]1([CH:8]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]#[C:30][Si](C)(C)C)[CH:24]=2)[CH2:9][N:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+]>CO>[C:29]([C:25]1[CH:24]=[C:23]([CH:8]([C:2]2([OH:1])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]2)[CH2:9][N:10]2[CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][CH2:15]2)[CH:28]=[CH:27][CH:26]=1)#[CH:30]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 68855543Tert-butyl 4-(2-(1-hydroxycyclohexyl)-2-{3-[(trimethylsilyl)ethynyl]phenyl}ethyl)piperazine-1-carboxylate

Product 1

HCID 86599048Tert-butyl 4-[2-(3-ethynylphenyl)-2-(1-hydroxycyclohexyl)ethyl]piperazine-1-carboxylateYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 4-(2-(1-hydroxycyclohexyl)-2-{3-[(trimethylsilyl)ethynyl]phenyl}ethyl)piperazine-1-carboxylate (104 mg, 0.215 mmol) in methanol (3 mL) was added potassium carbonate (300 mg, 2.17 mmol) and the mixture was stirred for 30 min at room temperature. The reaction mixture was quenched with aqueous ammonium chloride (5 mL) and extracted with ethyl acetate. The organic layer was washed with water, brine, dried (sodium sulfate), filtered and concentrated to give a crude oil, which was purified via silica gel flash chromatography (gradient from 10% ethyl acetate/hexane to 30% ethyl acetate/hexane) to yield 70 mg (80%) tert-butyl 4-[2-(3-ethynylphenyl)-2-(1-hydroxycyclohexyl)ethyl]piperazine-1-carboxylate as a white solid. MS (ESI) m/z 413 ([M+H]+); HRMS: calcd for C25H36N2O3+H, 413.2804; found (ESI, [M+H]+), 413.2809.

Workup

  1. customThe reaction mixture was quenched with aqueous ammonium chloride (5 mL)
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a crude oil, which
  8. customwas purified via silica gel flash chromatography (gradient from 10% ethyl acetate/hexane to 30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e4c664a761a64e7996574d7d997015dd
Source dataset
uspto-grants-2009_06
Patent number
US07550456B2

Reaction notes

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