tert-Butyl piperazine-1-carboxylate → HCID 66691662, 화합물

HRID 1808880노트

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HRID 1808880 반응식
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[C:15]1[CH:16]=[CH:17][C:18]([CH3:29])=[C:19]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH:20]=1.CCOC(C)=O.C(Cl)Cl>C1(C)C=CC=CC=1.C(O[Pd]OC(=O)C)(=O)C.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>[C:24]([O:23][C:22]([NH:21][C:19]1[CH:20]=[C:15]([N:4]2[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]2)[CH:16]=[CH:17][C:18]=1[CH3:29])=[O:28])([CH3:27])([CH3:26])[CH3:25]

참가 물질

7

반응물 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 10779535tert-Butyl (5-bromo-2-methylphenyl)carbamateHCID 21226138Dichloromethane ethylacetate

생성물 1

HCID 66691662HCID 66691662, 화합물수율 65.3%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl촉매HCID 1140Toluene용매

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온도
105 °C

실험 절차

A mixture of tert-butyl piperazine-1-carboxylate (5.47 g, 29.4 mmol), tert-butyl 5-bromo-2-methylphenylcarbamate (2.8 g, 9.78 mmol), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.233 g, 0.489 mmol), diacetoxypalladium (0.066 g, 0.294 mmol), and Reactant 5 (9.56 g, 29.4 mmol) (Cs2CO3) in Toluene (45 mL) was heated at 100-110° C. for 2 days. After the solvent was removed, the residue was dissolved in ethyl acetate and washed with water. After the EtOAc was removed, the residue was purified by column with DCM, then EtOAc/DCM (2%) to give tert-butyl 4-(3-(tert-butoxycarbonylamino)-4-methylphenyl)piperazine-1-carboxylate (2.5 g, 6.39 mmol, 65.3% yield, white solid). 1H-NMR (CDCl3, 500 MHz): δ 7.57 (1H, s), 7.00 (1H, d, J=8.55 Hz), 6.55 (1H, d, J=8.24 Hz), 6.31 (1H, s), 3.56 (4H, m), 3.09 (4H, m), 2.15 (3H, s), 1.52 (9H, s), 1.48 (9H, s).

후처리

  1. customAfter the solvent was removed
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with water
  4. customAfter the EtOAc was removed
  5. customthe residue was purified by column with DCM

출처 및 근거

ORD 기록
ord-e9e088eed382475a90bbce1cd7b2af62
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362004B2

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