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

HRID 971363Notes

Reaction equation

HRID 971363 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-5217be9ad6c447daaf0f0b8141abcd9f
Source dataset
uspto-grants-2007_12
Patent number
US07312246B2

Reaction notes

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