Sodium Bicarbonate → HCID 86649011、化合物

HRID 518095ノート

反応式

HRID 518095 の反応式
[Cl:1][C:2]1[C:3]([CH:16]=O)=[N:4][CH:5]=[C:6]([N:8]2[CH2:12][CH2:11][CH2:10][CH:9]2[CH2:13][O:14][CH3:15])[N:7]=1.[CH2:18]([NH:25][CH2:26][C@@H:27]([OH:31])[CH2:28][O:29][CH3:30])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(#N)C.C(O)(=O)C>[CH2:18]([N:25]([CH2:16][C:3]1[C:2]([Cl:1])=[N:7][C:6]([N:8]2[CH2:12][CH2:11][CH2:10][CH:9]2[CH2:13][O:14][CH3:15])=[CH:5][N:4]=1)[CH2:26][C@@H:27]([OH:31])[CH2:28][O:29][CH3:30])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

参加物

7

反応物 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 34179216HCID 34179216、化合物HCID 866490103-Chloro-5-[2-(methoxymethyl)pyrrolidin-1-yl]pyrazine-2-carbaldehyde

生成物 1

HCID 86649011HCID 86649011、化合物収率 67.1%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 6342Acetonitrile溶媒

実験手順

To a solution of 3-chloro-5-[2-(methoxymethyl)pyrrolidin-1-yl]pyrazine-2-carbaldehyde (511 mg), (2R)-1-(benzylamino)-3-methoxypropan-2-ol (469 mg) and acetic acid (343 μL) in acetonitrile (10 mL) was added sodium triacetoxyborohydride (636 mg), and the mixture was stirred at room temperature for 14.5 hr. To the reaction mixture was added dropwise a saturated sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (solvent gradient: 10→50% ethyl acetate/hexane) to give the title compound (583 mg, 67%).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (solvent gradient: 10→50% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-19f629b6ff904ae39fe9b5c2052264d3
出典データセット
uspto-grants-2015_08
特許番号
US09115139B2

反応ノート

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