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

HRID 971092

反応式

HRID 971092 の反応式
[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]

参加物

9

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8900Heptane溶媒HCID 22635083Tetrahydrofuran toluene溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-841f4d3d7ddc4b06a2cb958094345a70
出典データセット
uspto-grants-2007_12
特許番号
US07312334B2

関連ノート

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