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Potassium Carbonate → {4-[(5-Chloro-3-methyl-pyridin-2-ylmethyl)-amino]-butyl}-cyclopropyl-carbamic acid tert-butyl ester

HRID 251069
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HRID 251069 반응식
[C:1]([O:5][C:6](=[O:16])[N:7]([CH2:11][CH2:12][CH2:13][CH2:14][NH2:15])[CH:8]1[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[Cl:17][C:18]1[CH:19]=[C:20]([CH3:26])[C:21]([CH:24]=O)=[N:22][CH:23]=1.C([O-])([O-])=O.[K+].[K+].[BH4-].[Na+].C([O-])(O)=O.[Na+]>CO>[C:1]([O:5][C:6](=[O:16])[N:7]([CH2:11][CH2:12][CH2:13][CH2:14][NH:15][CH2:24][C:21]1[C:20]([CH3:26])=[CH:19][C:18]([Cl:17])=[CH:23][N:22]=1)[CH:8]1[CH2:9][CH2:10]1)([CH3:4])([CH3:2])[CH3:3]
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참가 물질

7

반응물 5

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 67271617(4-Amino-butyl)-cyclopropylcarbamic acid tert-butyl esterHCID 722140555-Chloro-3-methylpicolinaldehyde

생성물 1

HCID 67272035{4-[(5-Chloro-3-methyl-pyridin-2-ylmethyl)-amino]-butyl}-cyclopropyl-carbamic acid tert-butyl ester
수율 44%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
0 °C

실험 절차

A mixture of (4-amino-butyl)-cyclopropyl-carbamic acid tert-butyl ester (0.228 g, 1.00 mmol), 5-chloro-3-methyl-pyridine-2-carbaldehyde (0.141 g, 1.00 mmol) and K2CO3 (0.138 g, 1.00) in MeOH (5 mL) was stirred for 16 h. The mixture was filtered through a celite cake and the filtrate was cooled at 0° C. NaBH4 (0.038 g, 1.0 mmol) was added to the filtrate, and the mixture was stirred for 30 min. Saturated aqueous NaHCO3 (20 mL) was added and MeOH was removed. The aqueous residue was extracted with CH2Cl2 (3×30 mL). The organic extracts were combined and dried over anhydrous Na2SO4. After filtration the solvent was removed by evaporation under vacuum, and the residue was purified by flash chromatography on a silica gel column (200:10:1 CH2Cl2/MeOH/NH4OH), affording {4-[(5-chloro-3-methyl-pyridin-2-ylmethyl)-amino]-butyl}-cyclopropyl-carbamic acid tert-butyl ester as a pale yellow oil (0.155 g, 44%). 1H NMR (CDCl3) δ 0.54-0.59 (m, 2H), 0.69-0.75 (m, 2H), 1.45 (s, 9H), 1.54-1.61 (m, 4H), 2.30 (s, 3H), 2.45-2.50 (m, 1H), 2.69-2.74 (m, 2H), 3.18-3.23 (m, 2H), 3.85 (s, 2H), 7.43 (s, 1H), 8.34 (s, 1H).

후처리

  1. filtrationThe mixture was filtered through a celite cake
  2. stirringthe mixture was stirred for 30 min
  3. customMeOH was removed
  4. extractionThe aqueous residue was extracted with CH2Cl2 (3×30 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationAfter filtration the solvent
  7. customwas removed by evaporation under vacuum
  8. customthe residue was purified by flash chromatography on a silica gel column (200:10:1 CH2Cl2/MeOH/NH4OH)

출처 및 근거

ORD 기록
ord-42800fbd41a2484e9a678f981631f29e
출처 데이터셋
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07863293B2

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