Hydrochloric Acid → HCID 57779818、化合物

HRID 552905ノート

反応式

HRID 552905 の反応式
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:14][C:13](=[O:15])[CH2:12][CH:11]3[O:16][C:17](=[O:19])[CH:18]=[C:10]23)=[CH:4][CH:3]=1.[BH4-].[Na+].Cl>CO>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:14][CH:13]([OH:15])[CH2:12][CH:11]3[O:16][C:17](=[O:19])[CH:18]=[C:10]23)=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 57779832HCID 57779832、化合物

生成物 1

HCID 57779818HCID 57779818、化合物

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

560 mg (1.61 mmol) of 4-[(6-chloropyridin-3-yl)methyl]-6-oxo-5,6,7,7a-tetrahydrofuro[3,2-b]-pyridin-2(4H)-one (Ex. 1-14) are dissolved in 14 ml of methanol, and 45 mg (1.20 mmol) of sodium borohydride are added at 0° C. The reaction mixture is stirred at 0° C. for one hour. After addition of 7.2 ml of 5% strength hydrochloric acid, the mixture is extracted with ethyl acetate. The organic phase is dried over sodium sulphate and concentrated under reduced pressure. Purification of the residue by column chromatography on silica gel (silica gel 60, Merck, particle size: 0.04 to 0.063 mm) using the solvent mixture dichloromethane:methanol (95:5) gives both possible diastereomers of 4-[(6-chloropyridin-3-yl)methyl]-6-hydroxy-5,6,7,7a-tetrahydrofuro-[3,2-b]pyridin-2(4H)-one: (a) 152 mg (34% of theory) of diastereomer A and (b) 63 mg (11% of theory) of diastereomer B.

後処理

  1. extractionthe mixture is extracted with ethyl acetate
  2. dry with materialThe organic phase is dried over sodium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customPurification of the residue by column chromatography on silica gel (silica gel 60, Merck, particle size: 0.04 to 0.063 mm)

出典と根拠

ORDレコード
ord-2df1d23300054021817847e94ae7fd15
出典データセット
uspto-grants-2011_05
特許番号
US07951951B2

反応ノート

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