tert-Butyl piperazine-1-carboxylate → HCID 71278847, compound

HRID 1749918Notes

Reaction equation

HRID 1749918 reaction equation
[C:1]([C:4]1[C:5]([OH:15])=[C:6]([CH:13]=O)[C:7]2[O:11][CH2:10][O:9][C:8]=2[CH:12]=1)(=[O:3])[CH3:2].[C:16]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[C:1]([C:4]1[C:5]([OH:15])=[C:6]([CH2:13][N:26]2[CH2:25][CH2:24][N:23]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:28][CH2:27]2)[C:7]2[O:11][CH2:10][O:9][C:8]=2[CH:12]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 86682043HCID 86682043, compound

Product 1

HCID 71278847HCID 71278847, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 6-acetyl-5-hydroxybenzo[d][1,3]dioxole-4-carboxaldehyde (0.14 g, 0.67 mmol) in methylene chloride (5.0 mL) was added with N-Boc-piperazine (0.13 g, 0.67 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 (0.14 g, 0.67 mmol). After completion of the addition, the mixture was stirred at room temperature for 3 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-[(6-acetyl-5-hydroxybenzo[d][1,3]dioxol-4-yl)methyl]piperazine-1-carboxylate (0.18 g, 71%).

Workup

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

Sources & evidence

ORD record
ord-f1ca052bdd0a4ba498066218473514a5
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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