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

HRID 380493노트

반응식

HRID 380493 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 183647941-t-Butoxycarbonyl-4-(4-fluorobenzyloxymethyl)piperidine수율 96.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-91d3ecf7f7794f2dba8c7928aa3d8acc
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06303593B1

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