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

HRID 1527342
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HRID 1527342 반응식
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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매
HCID 8028
Tetrahydrofuran
용매

실험 절차

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.

후처리

  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.

출처 및 근거

ORD 기록
ord-e6578c0ccc8846b79c8555e756973dc3
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09085555B2

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