N,N,N',N'-Tetramethylethylenediamine → (2-[(tert-Butoxycarbonyl)amino]pyridin-3-yl)boronic acid

HRID 1930757ノート

反応式

HRID 1930757 の反応式
[C:1]([O:5][C:6](=[O:14])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2].CN(C)CCN(C)C.C([Li])CCC.[B:28](OCC(C)C)([O:34]CC(C)C)[O:29]CC(C)C.[Cl-].[NH4+]>CCOCC.O1CCCC1>[C:1]([O:5][C:6]([NH:7][C:8]1[C:13]([B:28]([OH:34])[OH:29])=[CH:12][CH:11]=[CH:10][N:9]=1)=[O:14])([CH3:4])([CH3:2])[CH3:3]

参加物

8

反応物 5

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 25517Ammonium ChlorideHCID 61587Triisobutyl borateHCID 112063492-(Boc-amino)pyridineHCID 178418339Butyllithium

生成物 1

HCID 22135186(2-[(tert-Butoxycarbonyl)amino]pyridin-3-yl)boronic acid収率 71.4%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-70 °C

実験手順

A solution of tetrahydrofuran (400 mL) of pyridin-2-yl-carbamic acid tert-butyl ester (16 g) described in Manufacturing Example 1-7-1 and N,N,N′,N′-tetramethylethylene diamine (25 g) was cooled to −70° C., n-butyl lithium (78 mL, 2.64 M heptane solution) was added dropwise for 1 hour, and the mixture was stirred for 10 minutes. This mixture was then warmed to between −10° C. and −6° C., and stirred at that temperature for 2 hours. The solution was then cooled again to −70° C., and triisobutyl borate (58 g) was added dropwise for 1 hour. The mixture was warmed to 0° C., and saturated aqueous ammonium chloride solution was added thereto. To the resulting yellow solids was added ether and then stirred, and the solids were filtered and washed with ether and water. The solids were dried under a reduced pressure to obtain the title compound (14 g).

後処理

  1. temperatureThis mixture was then warmed to between −10° C. and −6° C.
  2. stirringstirred at that temperature for 2 hours
  3. temperatureThe solution was then cooled again to −70° C.
  4. temperatureThe mixture was warmed to 0° C.
  5. stirringstirred
  6. filtrationthe solids were filtered
  7. washwashed with ether and water
  8. customThe solids were dried under a reduced pressure

出典と根拠

ORDレコード
ord-0bdc8ad9c7b54110a1c9860c9ef7b31f
出典データセット
uspto-grants-2012_05
特許番号
US08188119B2

反応ノート

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