Lithium borohydride → [6-(4-Hydroxy-2-hydroxymethyl-pyrrolidin-1-yl)-6-oxo-hexyl]-carbamic Acid Benzyl Ester

HRID 1055772

反応式

HRID 1055772 の反応式
[BH4-].[Li+].C[O:4][C:5]([CH:7]1[CH2:11][CH:10]([OH:12])[CH2:9][N:8]1[C:13](=[O:30])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])=O>O1CCCC1.CO.C(Cl)(Cl)Cl>[CH2:23]([O:22][C:20](=[O:21])[NH:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][C:13]([N:8]1[CH2:9][CH:10]([OH:12])[CH2:11][CH:7]1[CH2:5][OH:4])=[O:30])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

参加物

5

反応物 2

HCID 4148881Lithium borohydrideHCID 686360711-(6-Benzyloxycarbonylamino-hexanoyl)-4-hydroxy-pyrrolidine-2-carboxylic Acid Methyl Ester

生成物 1

HCID 68638015[6-(4-Hydroxy-2-hydroxymethyl-pyrrolidin-1-yl)-6-oxo-hexyl]-carbamic Acid Benzyl Ester

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 21584188Chloroform methanol溶媒

反応条件

温度
0 °C

実験手順

To the solution of lithium borohydride (1.34 g) in anhydrous tetrahydrofuran (50 mL) was added a solution of methyl ester 2a in THF (50 mL) over a period of 30 mins at 0° C. After the addition the reaction mixture was brought to room temperature and stirred further under argon. The completion of the reaction was ascertained by TLC after 4 h. (Rf=0.4 in 10% MeOH/CHCl3). The reaction mixture was evaporated to dryness and cooled to 0° C. To the residue 3N HCl (100 mL) was added slowly. After stirring for 30 mins the product was extracted with dichloromethane (3×100 mL). The combined organic layer was washed with brine and dried over sodium sulfate. Organic layer was filtered and evaporated to dryness. Compound 3a was purified by column chromatography first by eluting with ethyl acetate to remove impurities followed by dichloromethane/methanol (5%) gave 14.3 g (70%)

後処理

  1. additionAfter the addition the reaction mixture
  2. customwas brought to room temperature
  3. customThe reaction mixture was evaporated to dryness
  4. additionTo the residue 3N HCl (100 mL) was added slowly
  5. stirringAfter stirring for 30 mins the product
  6. extractionwas extracted with dichloromethane (3×100 mL)
  7. washThe combined organic layer was washed with brine
  8. dry with materialdried over sodium sulfate
  9. filtrationOrganic layer was filtered
  10. customevaporated to dryness
  11. customCompound 3a was purified by column chromatography first
  12. washby eluting with ethyl acetate
  13. customto remove impurities
  14. customgave 14.3 g (70%)

出典と根拠

ORDレコード
ord-5d2406645c44431db78eccfd74a1d60b
出典データセット
uspto-grants-2016_07
特許番号
US09394540B2

関連ノート

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