tert-Butyl piperazine-1-carboxylate → HCID 86693001, compound

HRID 2173153Notes

Reaction equation

HRID 2173153 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][CH:13]=O)=[CH:9][CH:10]=2)[CH:5]=[CH:4][O:3]1.[N:15]1([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][CH2:13][N:18]3[CH2:17][CH2:16][N:15]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:20][CH2:19]3)=[CH:9][CH:10]=2)[CH:5]=[CH:4][O:3]1

Participants

5

Reactant 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 77230658(1-oxo-1H-isochromen-6-yl)acetaldehyde

Product 1

HCID 86693001HCID 86693001, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

(1-oxo-1H-isochromen-6-yl) acetaldehyde (240 mg, 1.275 mmol) and tert-butyl piperazine-1-carboxylate (238 mg, 1.275 mmol) were dissolved in dichloroethane (10 mL) and added sodium triacetoxyborohydride (811 mg, 3.83 mmol) then stirred at RT for 16 hrs. LC-MS showed product peak. The reaction was washed with NaHCO3, brine, dried over Na2SO4 and evaporated to dryness. The residue was chromatographed through a 80 g. ISCO Redi-Sep column and eluted with 0-100% ethyl acetate/hexane to yield tert-butyl 4-[2-(1-oxo-1H-isochromen-6-yl)ethyl]piperazine-1-carboxylate. 1H-NMR (500 MHz, CDCl3) δ ppm 8.25 (d, J=8 Hz, 1H), 7.42 (d, J=9.4 Hz, 2H), 6.49 (d, J=5.7 Hz, 1H), 3.49 (s, 4H), 2.96 (t, J=7.6 Hz, 2H), 2.69 (t, J=7.3 Hz, 2H), 2.51 (s, 4H), 1.50 (s, 9H).

Workup

  1. washThe reaction was washed with NaHCO3, brine
  2. dry with materialdried over Na2SO4
  3. customevaporated to dryness
  4. customThe residue was chromatographed through a 80 g
  5. washISCO Redi-Sep column and eluted with 0-100% ethyl acetate/hexane

Sources & evidence

ORD record
ord-eab4f764bed34b0a82ea9ace807c03b3
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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