Chloroform → Tert-butyl 2-(4-aminophenyl)pyrrolidine-1-carboxylate

HRID 2236507

반응식

HRID 2236507 반응식
[Li+].C[Si]([N-:6][Si](C)(C)C)(C)C.C(Cl)(Cl)Cl.P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.[H+].[B-](F)(F)(F)F.[C:34]([O:38][C:39]([N:41]1[CH2:45][CH2:44][CH2:43][CH:42]1[C:46]1[CH:51]=[CH:50][C:49](Br)=[CH:48][CH:47]=1)=[O:40])([CH3:37])([CH3:36])[CH3:35]>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].C1(C)C=CC=CC=1>[C:34]([O:38][C:39]([N:41]1[CH2:45][CH2:44][CH2:43][CH:42]1[C:46]1[CH:51]=[CH:50][C:49]([NH2:6])=[CH:48][CH:47]=1)=[O:40])([CH3:37])([CH3:36])[CH3:35]

참가 물질

8

반응물 5

HCID 6212ChloroformHCID 28118Tetrafluoroboric acidHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 2733832Lithium HexamethyldisilazideHCID 53407516tert-Butyl 2-(4-bromophenyl)pyrrolidine-1-carboxylate

생성물 1

HCID 44607625Tert-butyl 2-(4-aminophenyl)pyrrolidine-1-carboxylate수율 83%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

실험 절차

LiHMDS (1.6 g, 9.6 mmol) is added to a 100 mL round bottom flask. Toluene (20 mL) is added followed by addition of Pd2(dba)3.CHCl3 (50 mg, 0.05 mmol) and P(tBu)3.HBF4 (40 mg, 0.14 mmol). 2-(4-Bromo-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (1.5 g, 4.6 mmol) is added to the flask. After degasing, the mixture is stirred at room temperature overnight. After TLC suggested no starting bromide is left, the reaction mixture is diluted with ether and poured into dilute HCl (aq). The ether layer is discarded, the aqueous layer is basified with NH4OH and extracted with EtOAc. The EtOAc layer is dried and concentrated to provide the desired product (1.0 g, 83%). 1H NMR (300 MHz, CDCl3) ∂ 6.94-6.96 (2H, m), 6.60-6.67 (2H, m), 4.67-4.85 (1H, m), 3.58 (4H, br), 2.24 (1H, m), 1.73-1.97 (3H, m), 1.44 (3H, s), 1.21 (6H, s).

후처리

  1. customAfter degasing
  2. waitis left
  3. additionthe reaction mixture is diluted with ether
  4. additionpoured into dilute HCl (aq)
  5. extractionextracted with EtOAc
  6. dry with materialThe EtOAc layer is dried
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-791a14add560472c9c4d37d86e6eb5b9
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07713994B2

연결된 노트

불러오는 중…