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Hydrochloric Acid → 1'-(4-Amino-3-methoxy-phenyl)-[4,4']bipiperidinyl-1-carboxylic acid tert-butyl ester

HRID 604291
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HRID 604291 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]2[CH2:19][CH2:18][N:17]([C:20]3[CH:25]=[CH:24][C:23]([N+:26]([O-])=O)=[C:22]([O:29][CH3:30])[CH:21]=3)[CH2:16][CH2:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.C(OCC)(=O)C>C(O)C.[Fe]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]2[CH2:19][CH2:18][N:17]([C:20]3[CH:25]=[CH:24][C:23]([NH2:26])=[C:22]([O:29][CH3:30])[CH:21]=3)[CH2:16][CH2:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
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6

반응물 3

HCID 313Hydrochloric Acid2회HCID 8857Ethyl AcetateHCID 598602671'-(3-Methoxy-4-nitro-phenyl)-[4,4']bipiperidinyl-1-carboxylic acid tert-butyl ester

생성물 1

HCID 598492031'-(4-Amino-3-methoxy-phenyl)-[4,4']bipiperidinyl-1-carboxylic acid tert-butyl ester수율 95.3%

시약·촉매·용매 2

HCID 23925Iron촉매
HCID 702Ethanol용매

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온도
80 °C

실험 절차

A mixture of 1′-(3-Methoxy-4-nitro-phenyl)-[4,4′]bipiperidinyl-1-carboxylic acid tert-butyl ester (2.0 g, 4.77 mmol), iron powder (1.33 g, 23.85 mmol), 1N hydrogen chloride (9.54 mL, 9.54 mmol) in ethanol (50 mL) is stirred at 80° C. for 3 h. After cooling to room temperature, 2N hydrogen chloride (5 mL) and ethyl acetate are added and then the mixture is filtrated. After concentration in vacuo, the mixture is extracted with AcOEt, washed with brine, dried over sodium sulfate and evaporated to give 1′-(4-Amino-3-methoxy-phenyl)-[4,4′]bipiperidinyl-1-carboxylic acid tert-butyl ester (1.77 g, 95% yield) as pale purple solids.

후처리

  1. temperatureAfter cooling to room temperature
  2. filtrationthe mixture is filtrated
  3. concentrationAfter concentration in vacuo
  4. extractionthe mixture is extracted with AcOEt
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated

출처 및 근거

ORD 기록
ord-b5e3df4643304464ac7317b766b395ae
출처 데이터셋
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07910585B2

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