Potassium Phosphate, Tribasic → tert-Butyl ((trans)-2-(4-cyclopropylphenyl)cyclopropyl)carbamate

HRID 529366노트

반응식

HRID 529366 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:10][C@H:9]2[NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:4][CH:3]=1.[CH:19]1(B(O)O)[CH2:21][CH2:20]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C1(C)C=CC=CC=1>[CH:19]1([C:2]2[CH:7]=[CH:6][C:5]([C@@H:8]3[CH2:10][C@H:9]3[NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:4][CH:3]=2)[CH2:21][CH2:20]1

참가 물질

8

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 86658779tert-butyl ((1R,2S)-2-(4-bromophenyl)cyclopropyl)carbamate

생성물 1

HCID 86708265tert-Butyl ((trans)-2-(4-cyclopropylphenyl)cyclopropyl)carbamate수율 76.2%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

To a 30-mL microwave tube were added tert-butyl (trans-2-(4-bromophenyl)cyclopropyl)carbamate (400 mg, 1.281 mmol), cyclopropylboronic acid (143 mg, 1.666 mmol), potassium phosphate (952 mg, 4.48 mmol), tricyclohexylphosphine (35.9 mg, 0.128 mmol), toluene (4 mL) and water (0.2 mL), and the mixture was degassed by bubbling N2. Palladium(II) acetate (14.38 mg, 0.064 mmol) was added and the tube was sealed. The mixture was heated at 100° C. with stirring for 4 h. The mixture was cooled and quenched with water (5 mL) and extracted with EtOAc (3×). The extract was dried (Na2SO4) and concentrated. The residue was purified using column chromatography (silica gel, 0 to 70% EtOAc/hexanes) to give 267 mg of product as pale yellow solid. MS: (M+H)+=274.2. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.61-0.73 (m, 2H), 0.90-1.01 (m, 2H), 1.08-1.24 (m, 2H), 1.42-1.52 (s, 9H), 1.81-1.94 (m, 1H), 1.98-2.12 (m, 1H), 2.70 (br. s., 1H), 6.91-7.12 (m, 4H).

후처리

  1. customthe mixture was degassed
  2. customby bubbling N2
  3. customthe tube was sealed
  4. temperatureThe mixture was cooled
  5. customquenched with water (5 mL)
  6. extractionextracted with EtOAc (3×)
  7. dry with materialThe extract was dried (Na2SO4)
  8. concentrationconcentrated
  9. customThe residue was purified

출처 및 근거

ORD 기록
ord-9c3fafdd5ae248e489e94b595a8c45a4
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346840B2

반응 노트

불러오는 중…