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tert-Butyl piperazine-1-carboxylate → HCID 71278847, 화합물

HRID 1749918
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HRID 1749918 반응식
[C:1]([C:4]1[C:5]([OH:15])=[C:6]([CH:13]=O)[C:7]2[O:11][CH2:10][O:9][C:8]=2[CH:12]=1)(=[O:3])[CH3:2].[C:16]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[C:1]([C:4]1[C:5]([OH:15])=[C:6]([CH2:13][N:26]2[CH2:25][CH2:24][N:23]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:28][CH2:27]2)[C:7]2[O:11][CH2:10][O:9][C:8]=2[CH:12]=1)(=[O:3])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 86682043HCID 86682043, 화합물

생성물 1

HCID 71278847HCID 71278847, 화합물수율 71%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of 6-acetyl-5-hydroxybenzo[d][1,3]dioxole-4-carboxaldehyde (0.14 g, 0.67 mmol) in methylene chloride (5.0 mL) was added with N-Boc-piperazine (0.13 g, 0.67 mmol), and the mixture was stirred at room temperature for 10 minutes. The reaction mixture was cooled to 0° C., and then added portionwise with sodium triacetoxyborohydride (0.14 g, 0.67 mmol). After completion of the addition, the mixture was stirred at room temperature for 3 hours. The reaction mixture was added with methylene chloride, and the organic layer was washed successively with water and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was subjected to silica gel column chromatography (eluted with hexane/ethyl acetate (2:1→3:7)) to obtain tert-butyl 4-[(6-acetyl-5-hydroxybenzo[d][1,3]dioxol-4-yl)methyl]piperazine-1-carboxylate (0.18 g, 71%).

후처리

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. additionAfter completion of the addition
  3. stirringthe mixture was stirred at room temperature for 3 hours
  4. washthe organic layer was washed successively with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. washthe residue was subjected to silica gel column chromatography (eluted with hexane/ethyl acetate (2:1→3:7))

출처 및 근거

ORD 기록
ord-f1ca052bdd0a4ba498066218473514a5
출처 데이터셋
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09156827B2

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