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

HRID 25850

반응식

HRID 25850 반응식
[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]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile2회HCID 15023839(S)-2-IsopropylpiperazineHCID 21226129Dichloromethane methanol

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매2회HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-d95c0cf80dc140a8b7f0457decee3580
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06858600B2

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