tert-Butyl piperazine-1-carboxylate → HCID 86682040, compound

HRID 1749913Notes

Reaction equation

HRID 1749913 reaction equation
[C:1]([C:4]1[C:5]([OH:16])=[C:6]([C:9]([O:14][CH3:15])=[C:10]([O:12][CH3:13])[CH:11]=1)[CH:7]=O)(=[O:3])[CH3:2].[C:17]([N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[C:1]([C:4]1[C:5]([OH:16])=[C:6]([C:9]([O:14][CH3:15])=[C:10]([O:12][CH3:13])[CH:11]=1)[CH2:7][N:27]1[CH2:26][CH2:25][N:24]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:29][CH2:28]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 86682039HCID 86682039, compound

Product 1

HCID 86682040HCID 86682040, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-acetyl-2-hydroxy-5,6-dimethoxybenzaldehyde (0.14 g, 0.63 mmol) in methylene chloride (5.0 mL) was added with N-Boc-piperazine (0.13 g, 0.70 mmol), and the mixture was stirred at room temperature for 10 minutes. The reaction mixture was cooled to 0° C., and then added portionwise with sodium triacetoxyborohydride (0.16 g, 0.76 mmol). After completion of the addition, the reaction mixture was warmed to room temperature, and stirred for 10 hours. The reaction mixture was added with methylene chloride, and the organic layer was washed successively with water and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was subjected to silica gel column chromatography (eluted with hexane/ethyl acetate (2:1→3:7)) to obtain tert-butyl 4-(3-acetyl-2-hydroxy-5,6-dimethoxybenzyl)piperazine-1-carboxylate (0.20 g, 80%).

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. additionAfter completion of the addition
  3. temperaturethe reaction mixture was warmed to room temperature
  4. stirringstirred for 10 hours
  5. washthe organic layer was washed successively with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. washthe residue was subjected to silica gel column chromatography (eluted with hexane/ethyl acetate (2:1→3:7))

Sources & evidence

ORD record
ord-2d3ad9f854ce49738f94e16ffcc1b3d2
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

Loading…