Sodium Hydroxide → tert-Butyl (3S)-3-benzylpiperazine-1-carboxylate

HRID 971367Notes

Reaction equation

HRID 971367 reaction equation
[OH-:1].[Na+].[CH2:3]([C@H:10]1[CH2:15][NH:14][CH2:13][CH2:12][NH:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(Cl)Cl.[CH3:19][OH:20]>C(O)(C)(C)C.O>[C:4]([O:1][C:19]([N:14]1[CH2:13][CH2:12][NH:11][C@@H:10]([CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:15]1)=[O:20])([CH3:9])([CH3:5])[CH3:3]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 20760001(S)-2-BenzylpiperazineHCID 21226129Dichloromethane methanol

Product 1

HCID 24820349tert-Butyl (3S)-3-benzylpiperazine-1-carboxylateYield 82.87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
0 °C

Procedure

6.67 ml (16.68 mmol, 1.00 eq.) of a 2.5 N aq. NaOH-solution were added to a solution of 2.94 g (16.68 mmol) 2-(S)-Benzyl-piperazine in 80 ml tert-Butanol and 80 ml H2O. After cooling to 0° C. 3.64 g (16.68 mmol, 1.00 eq.) Boc-anhydride was added and the mixture was stirred at 0° C. for 2 h. Then the solution was warmed to r.t. and stirred overnight. After evaporating the tert-Butanol the mixture was extracted with CH2Cl2. The comb. org. fractions were dried over Na2SO4 and evaporated. Column chromatography (CH2Cl2/MeOH (10+1)) yielded 3.82 g (13.82 mmol, 82.87%) 3-(S)-Benzyl-piperazine-1-carboxylic acid tert-butyl ester as a clear oil.

Workup

  1. temperatureThen the solution was warmed to r.t.
  2. stirringstirred overnight
  3. customAfter evaporating the tert-Butanol the mixture
  4. extractionwas extracted with CH2Cl2
  5. dry with materialfractions were dried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-83c7026db9b14b1890cfa197843508da
Source dataset
uspto-grants-2007_12
Patent number
US07312246B2

Reaction notes

Loading…