Sodium borohydride → 6-(5-hydroxymethyl-pyridin-3-yl)-1-methyl-3,4-dihydro-1H-[1,5]naphthyridin-2-one

HRID 1774798ノート

反応式

HRID 1774798 の反応式
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([C:10]2[CH:19]=[CH:18][C:17]3[N:16]([CH3:20])[C:15](=[O:21])[CH2:14][CH2:13][C:12]=3[N:11]=2)[CH:7]=[N:6][CH:5]=1.[BH4-].[Na+]>CO>[OH:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]2[N:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]([CH3:20])[C:15](=[O:21])[CH2:14][CH2:13]3)[CH:7]=[N:6][CH:5]=1

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 866791615-(5-Methyl-6-oxo-5,6,7,8-tetrahydro-[1,5]naphthyridin-2-yl)-nicotinic acid methyl ester

生成物 1

HCID 866791626-(5-hydroxymethyl-pyridin-3-yl)-1-methyl-3,4-dihydro-1H-[1,5]naphthyridin-2-one収率 77.6%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a stirred solution of 5-(5-methyl-6-oxo-5,6,7,8-tetrahydro-[1,5]naphthyridin-2-yl)-nicotinic acid methyl ester (270 mg, 0.91 mmol) in MeOH (10 mL) was added sodium borohydride (300 mg, 8.0 mmol) at RT. After stirring overnight, the reaction mixture was quenched by adding water (5.0 mL). It was then concentrated in vacuo to give a light yellow oil. After extraction with EtOAc, the organic layer was washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give 6-(5-hydroxymethyl-pyridin-3-yl)-1-methyl-3,4-dihydro-1H-[1,5]naphthyridin-2-one (190 mg, 77.6%) as a white solid. MS: 270.1 (M+H+).

後処理

  1. customthe reaction mixture was quenched
  2. additionby adding water (5.0 mL)
  3. concentrationIt was then concentrated in vacuo
  4. customto give a light yellow oil
  5. extractionAfter extraction with EtOAc
  6. washthe organic layer was washed with brine
  7. customdried over anhy
  8. filtrationNa2SO4, filtered
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-4da4bbcca8cb4bd9b732b932010d8649
出典データセット
uspto-grants-2016_02
特許番号
US09260408B2

反応ノート

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