Water → 1-t-Butoxycarbonyl-4-(4-fluorobenzyloxymethyl)piperidine

HRID 380493ノート

反応式

HRID 380493 の反応式
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][CH:20]([CH2:23][OH:24])[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].[H-].[Na+].O>C1COCC1>[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][CH:20]([CH2:23][O:24][CH2:6][C:5]2[CH:8]=[CH:9][C:2]([F:1])=[CH:3][CH:4]=2)[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11]

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 680214-Fluorobenzyl bromideHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

生成物 1

HCID 183647941-t-Butoxycarbonyl-4-(4-fluorobenzyloxymethyl)piperidine収率 96.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 0.75 g (6.02 mmol) of 4-fluorobenzylbromide and 0.58 g (2.7 mmol) of 1-t-butoxycarbonyl-4-hydroxymethylpiperidine in 5 mL of THF was added 0.136 g (5.4 mmol) of NaH in 3 portions over 30 min. After 3.5 h, 50 mL of H2O was added to the reaction mixture and it was extracted with ethyl acetate. The combined organic fractions were washed with sat'd Nacl solution, dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, hexanes:ethyl aceate, 4:1) to give 0.84 g of the title compound.

後処理

  1. extractionwas extracted with ethyl acetate
  2. washThe combined organic fractions were washed with sat'd Nacl solution
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by chromatography (silica, hexanes:ethyl aceate, 4:1)

出典と根拠

ORDレコード
ord-91d3ecf7f7794f2dba8c7928aa3d8acc
出典データセット
uspto-grants-2001_10
特許番号
US06303593B1

反応ノート

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