Acetic Acid → HCID 46785855, compound

HRID 2066544Notes

Reaction equation

HRID 2066544 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[C:15]([OH:18])(=O)[CH3:16].C([BH3-])#N.[Na+].[CH2:23]1[CH2:27]OC[CH2:24]1>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:24]2[CH2:16][CH2:15][O:18][CH2:27][CH2:23]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 962WaterHCID 8028TetrahydrofuranHCID 143452tert-Butyl piperazine-1-carboxylateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 46785855HCID 46785855, compoundYield 25%

Conditions

Temperature
60 °C

Procedure

To a solution of piperazine-1-carboxylic acid tert-butyl ester (1.5 g, 8.05 mmol) stirring in anhydrous THF (20 mL) and water (0.2 mL) was added glacial acetic acid (1.45 mL, 24.2 mmol), followed by sodium cyanoborohydride (758 mg, 12.1 mmol). The reaction mixture was stirred at 60° C. for 12 h, quenched with 10% aqueous NaHCO3 (50 mL), extracted with EtOAc and dried (MgSO4) to give a colourless oil which was purified by silica chromatography to give 4-(tetrahydro-pyran-4-yl)-piperazine-1-carboxylic acid tert-butyl ester (0.54 g, 25%), as a white solid. BOC-deprotection was carried out as in Reference Example 3 to give the title compound (0.30 g, 88%).

Workup

  1. customquenched with 10% aqueous NaHCO3 (50 mL)
  2. extractionextracted with EtOAc
  3. dry with materialdried (MgSO4)
  4. customto give a colourless oil which
  5. customwas purified by silica chromatography

Sources & evidence

ORD record
ord-893db286c53f4106839b6bc0c1cffd7d
Source dataset
uspto-grants-2012_10
Patent number
US08293735B2

Reaction notes

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