Lithium borohydride → 3-Hydroxy-4-hydroxymethyl-pyrrolidine-1-carboxylic Acid Benzyl Ester

HRID 20921

反応式

HRID 20921 の反応式
[BH4-].[Li+].C([O:5][C:6]([CH:8]1[CH:12]([OH:13])[CH2:11][N:10]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH2:9]1)=O)C>O1CCCC1.CO.C(Cl)(Cl)Cl>[CH2:17]([O:16][C:14]([N:10]1[CH2:9][CH:8]([CH2:6][OH:5])[CH:12]([OH:13])[CH2:11]1)=[O:15])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

参加物

5

反応物 2

HCID 4148881Lithium borohydrideHCID 150432791-Benzyl 3-ethyl 4-hydroxypyrrolidine-1,3-dicarboxylate

生成物 1

HCID 230620493-Hydroxy-4-hydroxymethyl-pyrrolidine-1-carboxylic 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 (0.305 g, 13 mmol) in anhydrous tetrahydrofuran (25 mL) was added a solution of ethyl ester 73 (2.69 g, 9.2 mmol) in THF (25 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=0.3 in 10% MeOH/CHCl3). The reaction mixture was evaporated to dryness and cooled to 0° C. To the residue 3N HCl (40 mL) was added slowly. After stirring for 30 mins the product was extracted with dichloromethane (3×75 mL). The combined organic layer was washed with brine and dried over sodium sulfate. Organic layer was filtered and evaporated to dryness. Compound 74 was purified by column chromatography first by eluting with dichloromethane/methanol (5%) (1.98 g, 85%).

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 (40 mL) was added slowly
  5. stirringAfter stirring for 30 mins the product
  6. extractionwas extracted with dichloromethane (3×75 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 74 was purified by column chromatography first
  12. washby eluting with dichloromethane/methanol (5%) (1.98 g, 85%)

出典と根拠

ORDレコード
ord-4dbcce509f574c3b8a7be628670e9b46
出典データセット
uspto-grants-2010_06
特許番号
US07745608B2

関連ノート

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