Sodium triacetoxyborohydride → Tert-butyl 4-{2-[4-(1-methyl-6-oxo-1,6-dihydro-[4,4']bipyrimidinyl-2-yloxy)piperidin-1-yl]ethyl}piperidine-1-carboxylate

HRID 1468783

反応式

HRID 1468783 の反応式
[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[C:5]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][N:10]=2)[N:4]=[C:3]1[O:15][CH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.O=[CH:23][CH2:24][CH:25]1[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][CH2:26]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C.ClCCCl>[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[C:5]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][N:10]=2)[N:4]=[C:3]1[O:15][CH:16]1[CH2:21][CH2:20][N:19]([CH2:23][CH2:24][CH:25]2[CH2:26][CH2:27][N:28]([C:31]([O:33][C:34]([CH3:35])([CH3:37])[CH3:36])=[O:32])[CH2:29][CH2:30]2)[CH2:18][CH2:17]1

参加物

6

反応物 3

HCID 5049666Sodium triacetoxyborohydrideHCID 10353694tert-Butyl 4-(2-oxoethyl)piperidine-1-carboxylateHCID 679776501-methyl-2-(piperidin-4-yloxy)-1H-[4,4']bipyrimidinyl-6-one

生成物 1

HCID 68160052Tert-butyl 4-{2-[4-(1-methyl-6-oxo-1,6-dihydro-[4,4']bipyrimidinyl-2-yloxy)piperidin-1-yl]ethyl}piperidine-1-carboxylate収率 67%

試薬・触媒・溶媒 2

HCID 176Acetic Acid触媒HCID 111,2-Dichloroethane溶媒

実験手順

To a mixture of 1-methyl-2-(piperidin-4-yloxy)-1H-[4,4′]bipyrimidinyl-6-one (290 mg, 1.0 mmol), tert-butyl 4-(2-oxo-ethyl)piperidine-1-carboxylate (300 mg 1.3 mmol) and acetic acid (one drop) in 1,2-dichloroethane (5.0 ml) was added sodium triacetoxyborohydride (530 mg, 2.5 mmol). The mixture was stirred at room temperature overnight. The mixture was partitioned between water and dichloromethane. The organic layer was washed with brine, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by NH-silica gel column chromatography (eluent; hexane/ethyl acetate=30/70) to afford tert-butyl 4-{2-[4-(1-methyl-6-oxo-1,6-dihydro-[4,4′]bipyrimidinyl-2-yloxy)piperidin-1-yl]ethyl}piperidine-1-carboxylate as a colorless solid (340 mg, 0.67 mmol, 67%).

後処理

  1. customThe mixture was partitioned between water and dichloromethane
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by NH-silica gel column chromatography (eluent; hexane/ethyl acetate=30/70)

出典と根拠

ORDレコード
ord-d8ab29b0c53b4e918a83262e1607bd49
出典データセット
uspto-grants-2015_04
特許番号
US09006232B2

関連ノート

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