Lithium borohydride → tert-Butyl 4-fluoro-4-(hydroxymethyl)piperidine-1-carboxylate

HRID 401954ノート

反応式

HRID 401954 の反応式
C([O:3][C:4]([C:6]1([F:19])[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)=O)C.[Li+].[BH4-]>C1COCC1>[C:15]([O:14][C:12]([N:9]1[CH2:8][CH2:7][C:6]([F:19])([CH2:4][OH:3])[CH2:11][CH2:10]1)=[O:13])([CH3:18])([CH3:16])[CH3:17]

参加物

4

反応物 2

HCID 4148881Lithium borohydrideHCID 21306965Ethyl N-Boc-4-fluoropiperidine-4-carboxylate

生成物 1

HCID 22248400tert-Butyl 4-fluoro-4-(hydroxymethyl)piperidine-1-carboxylate収率 86.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of 4-fluoro-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester (0.9 mmol, 0.25 g), in anhydrous THF (3 mL) under N2 atmosphere, was added LiBH4 (2.0 mmol, 1.0 mL, 2N solution in THF) dropwise and reaction was stirred at room temperature for 10 h. The reaction was quenched with slow addition of water (1 mL) and the product was extracted with ethyl acetate (2×5 mL), Organic layer was washed with water, (5 mL), brine (5 mL), dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified on a SiO2 cartridge with 30% ethyl acetate in hexanes to provide 4-fluoro-4-hydroxymethyl-piperidine-1-carboxylic acid tert-butyl ester (0.182 g).

後処理

  1. customreaction
  2. customThe reaction was quenched with slow addition of water (1 mL)
  3. extractionthe product was extracted with ethyl acetate (2×5 mL), Organic layer
  4. washwas washed with water, (5 mL), brine (5 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified on a SiO2 cartridge with 30% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-12aeb3cda24d4e938b12bb9ccbb48570
出典データセット
uspto-grants-2014_06
特許番号
US08741900B2

反応ノート

読み込み中…