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Morpholine → 1-(4-Morpholin-4-yl-phenyl)-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester

HRID 1400043
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HRID 1400043 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]2[C:10]([C:14]3[CH:19]=[CH:18][C:17](Br)=[CH:16][CH:15]=3)([CH2:11]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[Na+].[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]2[C:10]([C:14]3[CH:19]=[CH:18][C:17]([N:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)=[CH:16][CH:15]=3)([CH2:11]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 8083MorpholineHCID 23676156Sodium t-butoxideHCID 53432548tert-Butyl 1-(4-bromophenyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate2회

생성물 1

HCID 498544201-(4-Morpholin-4-yl-phenyl)-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester수율 66%

시약·촉매·용매 3

HCID 634876Binap, (A+-)-
촉매
HCID 9811564Bis(dibenzylideneacetone)palladium촉매
HCID 1140Toluene용매

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온도
90 °C

실험 절차

To a solution of 1-(4-bromo-phenyl)-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester (Intermediate I, 680 mg, 2.01 mmol) in anhydrous toluene (20 mL) were added Pd2(dba)3 (4.6 mg, 0.005 mmol), BINAP (9.4 mg, 0.015 mmol), sodium tert-butoxide (232 mg, 2.41 mmol) and morpholine (0.2 mL, 2.21 mmol) at r.t. and reaction mixture was stirred at 90° C. for 4 h. Reaction mixture was then concentrated and crude product was purified by column chromatography (silica gel, 1:9 EtOAc:Pet. ether) to afford the title compound as white solid (456 mg, 66%).

후처리

  1. customreaction mixture
  2. customReaction mixture
  3. concentrationwas then concentrated
  4. customcrude product was purified by column chromatography (silica gel, 1:9 EtOAc:Pet. ether)

출처 및 근거

ORD 기록
ord-b4196dbc4de34646825f284afb328580
출처 데이터셋
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08906913B2

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