Triethylamine → (S)-1-Boc-3-isopropylpiperazine

HRID 25850

Reaction equation

HRID 25850 reaction equation
[CH:1]([C@H:4]1[CH2:9][NH:8][CH2:7][CH2:6][NH:5]1)([CH3:3])[CH3:2].[CH3:10][C:11]([O:14][C:15](ON=C(C1C=CC=CC=1)C#N)=[O:16])([CH3:13])[CH3:12].C(N(CC)CC)C.C(Cl)Cl.CO>O1CCOCC1.O>[C:11]([O:14][C:15]([N:8]1[CH2:7][CH2:6][NH:5][C@@H:4]([CH:1]([CH3:3])[CH3:2])[CH2:9]1)=[O:16])([CH3:13])([CH3:12])[CH3:10]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile2×HCID 15023839(S)-2-IsopropylpiperazineHCID 21226129Dichloromethane methanol

Product 1

HCID 24820348(S)-1-Boc-3-isopropylpiperazineYield 74.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

341 mg (2.66 mmol) 2-(S)-Isopropyl-piperazine (84) and 657 mg (2.67 mmol, 1.00 eq.) BOC-ON© (2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile) were dissolved in 20 ml 1,4-dioxane and 20 ml water. After adding 2.04 ml (14.64 mmol, 5.50 eq.) triethylamine the solution was stirred at r.t. for 24 h. Then the mixture was added to water and extracted with EtOAc. The comb. org. fractions were washed with brine, dried over Na2SO4 and evaporated. Column chromatography (CH2Cl2/MeOH (3+1)) yielded 454.9 mg (1.99 mmol, 74.90%) 3-(S)-Isopropyl-piperazine-1-carboxylic acid tert-butyl ester (85) as a clear oil.

Workup

  1. extractionextracted with EtOAc
  2. washfractions were washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-d95c0cf80dc140a8b7f0457decee3580
Source dataset
uspto-grants-2005_02
Patent number
US06858600B2

Linked notes

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