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Lithium Chloride → (2S,5R)-1-Benzyl-5-hydroxymethyl-pyrrolidine-2-carboxylic acid (3-trifluoromethoxy-phenyl)-amide

HRID 1527342
ノート
印刷プレビュー

反応式

HRID 1527342 の反応式
C([O:3][C:4]([C@H:6]1[CH2:10][CH2:9][C@@H:8]([C:11](=[O:24])[NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:20]([F:23])([F:22])[F:21])[CH:14]=2)[N:7]1[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=O)C.[Li+].[Cl-].[BH4-].[Na+]>C1COCC1.CCO>[F:22][C:20]([F:21])([F:23])[O:19][C:15]1[CH:14]=[C:13]([NH:12][C:11]([C@@H:8]2[CH2:9][CH2:10][C@H:6]([CH2:4][OH:3])[N:7]2[CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:24])[CH:18]=[CH:17][CH:16]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 68283977(2R,5S)-1-Benzyl-5-(3-trifluoromethoxy-phenylcarbamoyl)-pyrrolidine-2-carboxylic acid ethyl ester

生成物 1

HCID 71042580(2S,5R)-1-Benzyl-5-hydroxymethyl-pyrrolidine-2-carboxylic acid (3-trifluoromethoxy-phenyl)-amide

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒
HCID 8028
Tetrahydrofuran
溶媒

実験手順

To a solution of (2R,5S)-1-benzyl-5-(3-trifluoromethoxy-phenylcarbamoyl)-pyrrolidine-2-carboxylic acid ethyl ester (2.5 g, 5.73 mmol) in a mixture of THF (40 mL) and EtOH (20 mL) was added LiCl (486 mg, 11.5 mmol) followed by NaBH4 (451 mg, 11.5 mmol) and the mixture was stirred at RT overnight. The crude reaction mixture was concentrated, EtOAc and 1N HCl were added, the layers were separated and the aqueous one back-extracted with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated. The crude residue was used without further purification in the next step. MS (LC/MS): 395 [M+H]+; tR (HPLC conditions b): 3.66 min.

後処理

  1. customThe crude reaction mixture
  2. concentrationwas concentrated
  3. additionEtOAc and 1N HCl were added
  4. customthe layers were separated
  5. extractionthe aqueous one back-extracted with EtOAc
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude residue was used without further purification in the next step
  11. custom3.66 min.

出典と根拠

ORDレコード
ord-e6578c0ccc8846b79c8555e756973dc3
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09085555B2

反応ノート

読み込み中…

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