Lithium borohydride → tert-Butyl (2R,4R)-4-fluoro-2-(hydroxymethyl)pyrrolidine-1-carboxylate

HRID 732358노트

반응식

HRID 732358 반응식
[BH4-].[Li+].C[O:4][C:5]([C@H:7]1[CH2:11][C@@H:10]([F:12])[CH2:9][N:8]1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=O>C1COCC1>[C:16]([O:15][C:13]([N:8]1[CH2:9][C@H:10]([F:12])[CH2:11][C@@H:7]1[CH2:5][OH:4])=[O:14])([CH3:19])([CH3:18])[CH3:17]

참가 물질

4

반응물 2

HCID 4148881Lithium borohydrideHCID 68687525(2R,4R)-1-tert-butyl 2-methyl 4-fluoropyrrolidine-1,2-dicarboxylate

생성물 1

HCID 68815110tert-Butyl (2R,4R)-4-fluoro-2-(hydroxymethyl)pyrrolidine-1-carboxylate수율 80.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Add lithium borohydride (1.03 g, 47.4 mmol) to an ice cold solution of 4-(R)-fluoropyrrolidine-N1,2-(R)-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (7.8 g, 31.5 mmol) in THF (100 mL). Let warm to room temperature over 18 h. Cool in ice bath. Slowly add acetic acid (5 mL) and water and extract with ethyl acetate. Wash extract with water, saturated aqueous sodium bicarbonate solution, saturated aqueous sodium chloride, dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with hexanes and ethyl acetate) to give the title compound as a thick oil (5.56 g, 80%).

후처리

  1. temperatureCool in ice bath
  2. extractionSlowly add acetic acid (5 mL) and water and extract with ethyl acetate
  3. washWash
  4. extractionextract with water, saturated aqueous sodium bicarbonate solution, saturated aqueous sodium chloride
  5. dry with materialdry (magnesium sulfate)
  6. concentrationconcentrate
  7. custompurify
  8. wash(silica gel chromatography, eluting with hexanes and ethyl acetate)

출처 및 근거

ORD 기록
ord-f86f6e7cf5fe4df39bb4b58e4ba3e370
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07585885B2

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