tert-Butyl piperazine-1-carboxylate → HCID 66691662、化合物

HRID 1808880ノート

反応式

HRID 1808880 の反応式
[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]

参加物

7

反応物 3

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

生成物 1

HCID 66691662HCID 66691662、化合物収率 65.3%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl触媒HCID 1140Toluene溶媒

反応条件

温度
105 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e9e088eed382475a90bbce1cd7b2af62
出典データセット
uspto-grants-2013_01
特許番号
US08362004B2

反応ノート

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