2,6-Dibromopyridine → tert-Butyl 4-(6-bromopyridin-2-yl)-4-hydroxypiperidine-1-carboxylate

HRID 2039720ノート

反応式

HRID 2039720 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.C([Li])CCC.[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][C:24](=[O:27])[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15].[Cl-].[NH4+]>ClCCl>[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][C:24]([OH:27])([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=2)[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:15])[CH3:16]

参加物

6

反応物 4

HCID 122742,6-DibromopyridineHCID 25517Ammonium ChlorideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate2 回HCID 178418339Butyllithium

生成物 1

HCID 86614831tert-Butyl 4-(6-bromopyridin-2-yl)-4-hydroxypiperidine-1-carboxylate収率 98.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

As shown in FIG. 7—step i, to a solution of 2,6-dibromopyridine (4.738 g) in dichloromethane (80 mL) was added dropwise n-butyllithium (2.5 N, 8.9 mL) at or below −65° C., followed by stirring at this temperature for 20 min. 4-Oxo-piperidine-1-carboxylic acid tert-butyl ester (compound 1030) (4.38 g) was added. After 15 min, the temperature was brought up to −30° C. and a saturated aqueous ammonium chloride solution (100 mL) was added. The organic and aqueous layers were separated, the aqueous layer extracted with dichloromethane (2×80 mL). The combined organics were evaporated to gave a residue which was triturated with hexane to give 6-bromo-4′-hydroxy-3′,4′,5′,6′-tetrahydro-2′H-[2,4′]bipyridinyl-1′-carboxylic acid tert-butyl ester (compound 1031) as a white solid (7.05 g).

後処理

  1. waitAfter 15 min
  2. customwas brought up to −30° C.
  3. customThe organic and aqueous layers were separated
  4. extractionthe aqueous layer extracted with dichloromethane (2×80 mL)
  5. customThe combined organics were evaporated
  6. customto gave a residue which
  7. customwas triturated with hexane

出典と根拠

ORDレコード
ord-d91c675f6c1e4ac18b5423fedf646004
出典データセット
uspto-grants-2013_11
特許番号
US08580802B2

反応ノート

読み込み中…