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

HRID 732358ノート

反応式

HRID 732358 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-f86f6e7cf5fe4df39bb4b58e4ba3e370
出典データセット
uspto-grants-2009_09
特許番号
US07585885B2

反応ノート

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