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Triacetoxyperiodinane → 1-(4-(4-Methylphenyl)-piperazine-1-carbonyl)-cyclopentanecarbaldehyde

HRID 417997
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HRID 417997 반응식
[OH:1][CH2:2][C:3]1([C:8]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.CCOCC.[OH-].[Na+]>[CH3:22][C:19]1[CH:18]=[CH:17][C:16]([N:13]2[CH2:12][CH2:11][N:10]([C:8]([C:3]3([CH:2]=[O:1])[CH2:4][CH2:5][CH2:6][CH2:7]3)=[O:9])[CH2:15][CH2:14]2)=[CH:21][CH:20]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 2

HCID 159087TriacetoxyperiodinaneHCID 66651026(1-Hydroxymethyl-cyclopentyl)-(4-(4-methylphenyl)piperazin-1-yl)-methanone

생성물 1

HCID 866357821-(4-(4-Methylphenyl)-piperazine-1-carbonyl)-cyclopentanecarbaldehyde수율 105%

시약·촉매·용매 3

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매
HCID 14798
Sodium Hydroxide
용매

실험 절차

(1-Hydroxymethyl-cyclopentyl)-(4-(4-methylphenyl)piperazin-1-yl)-methanone from the previous step (1.57 g, 5.22 mmol) was dissolved in DCM (40 mL). Dess-Martin periodinane (3.06 g, 7.22 mmol) was added and the reaction mixture was stirred at room temperature for 3.5 hours. The reaction mixture diluted with Et2O (100 mL) and 1M aq NaOH solution (50 mL) was added. The reaction mixture was stirred for 20 minutes and then the organic layer was separated and washed with 1M aq NaOH solution (50 mL), water (50 mL), dried (MgSO4) and concentrated in vacuo to give 1-(4-(4-methylphenyl)-piperazine-1-carbonyl)-cyclopentanecarbaldehyde (1.64 g, 105%) as a brown oil which was used without further purification.

후처리

  1. additionwas added
  2. stirringThe reaction mixture was stirred for 20 minutes
  3. customthe organic layer was separated
  4. washwashed with 1M aq NaOH solution (50 mL), water (50 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-d0b34e02926f407f95cd2010c108d29b
출처 데이터셋
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08093248B2

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