Phosphoric Acid → (3-[4-(Tert-butoxycarbonyl)piperazin-1-YL]phenyl)boronic acid

HRID 971092

반응식

HRID 971092 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16](Br)[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.[B:26](OC(C)C)([O:31]C(C)C)[O:27]C(C)C.[Cl-].[NH4+].OP(O)(O)=O>O1CCCC1.C1(C)C=CC=CC=1.CCCCCCC.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[C:16]([B:26]([OH:31])[OH:27])[CH:17]=[CH:18][CH:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

9

반응물 5

HCID 1004Phosphoric AcidHCID 21531Triisopropyl borateHCID 25517Ammonium ChlorideHCID 10882380tert-Butyl 4-(3-bromophenyl)piperazine-1-carboxylateHCID 178418339Butyllithium

생성물 1

HCID 22392008(3-[4-(Tert-butoxycarbonyl)piperazin-1-YL]phenyl)boronic acid

시약·촉매·용매 3

HCID 962Water용매HCID 8900Heptane용매HCID 22635083Tetrahydrofuran toluene용매

반응 조건

온도
-78 °C

실험 절차

To the 4-tert-Butyloxycarbonyl-1-(3-bromophenyl)piperazine from Step 1 (118.30 g, 346.9 mmol) in tetrahydrofuran/toluene (1/1, 1.5 L) at −78° C. under nitrogen was added n-butyllithium (2.5M, 160 mL, 398.9 mmol) dropwise and the resulting reaction mixture was stirred at −78° C. for 20 minutes. Triisopropyl borate (96.4 mL, 416.3 mmol) was added dropwise and the reaction was warmed to 0° C. and stirred for 2 hours. Aqueous saturated ammonium chloride (400 mL), water (100 mL) and 1 equivalent of H3PO4 (20 mL) were added and the mixture was stirred for 15 minutes and then concentrated to a volume of approximately 200 mL (at which stage the mixture became bluish and a precipitate formed). The mixture was slowly diluted with heptane (800 mL) and the resulting suspension was stirred overnight. The suspension was filtered, the solid was washed with heptane and dried to afford the title boronic acid.

후처리

  1. customthe resulting reaction mixture
  2. temperaturethe reaction was warmed to 0° C.
  3. stirringstirred for 2 hours
  4. stirringthe mixture was stirred for 15 minutes
  5. concentrationconcentrated to a volume of approximately 200 mL (at which stage the mixture
  6. customa precipitate formed)
  7. stirringthe resulting suspension was stirred overnight
  8. filtrationThe suspension was filtered
  9. washthe solid was washed with heptane
  10. customdried

출처 및 근거

ORD 기록
ord-841f4d3d7ddc4b06a2cb958094345a70
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07312334B2

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