Hydrochloric Acid → Methyl 6-[(isopropoxycarbonyl)amino]indane-5-carboxylate

HRID 604617노트

반응식

HRID 604617 반응식
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][CH2:8]2)=[CH:4][C:3]=1[C:11]([O:13][CH3:14])=[O:12].NC1C=CC2CCCC=2C=1C(OC)=O.N1C=CC=CC=1.Cl[C:36]([O:38][CH:39]([CH3:41])[CH3:40])=[O:37].Cl>C(Cl)Cl>[CH:39]([O:38][C:36]([NH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][CH2:8]2)=[CH:4][C:3]=1[C:11]([O:13][CH3:14])=[O:12])=[O:37])([CH3:41])[CH3:40]

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7917Isopropyl chloroformateHCID 59379136methyl 6-amino-2,3-dihydro-1H-indene-5-carboxylateHCID 67057733Methyl 5-aminoindane-4-carboxylate

생성물 1

HCID 59003158Methyl 6-[(isopropoxycarbonyl)amino]indane-5-carboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of a mixture of methyl 6-aminoindane-5-carboxylate and methyl 5-aminoindane-4-carboxylate (760 mg, 3.98 mmol), and pyridine (805 uL, 9.95 mmol) in CH2Cl2 (8 mL) at 0° C. under N2 was added isopropyl chloroformate (1 M in toluene) (3.98 mL, 3.98 mmol). The resulting mixture was stirred at room temperature for 16 h. 1M HCl was added to the reaction mixture and the organic layer was separated. The aqueous layer was extracted with CH2Cl2 (2×). The combined organic layers were dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography (Si, hexanes/EtOAc) to afford methyl 6-[(isopropoxycarbonyl)amino]indane-5-carboxylate. LCMS calc.=300.1; found=299.9 (M+Na)+. 1H NMR (500 MHz, CDCl3) δ 10.43 (s, 1H); 8.34 (s, 1H); 7.86 (s, 1H); 5.06-5.00 (m, 1H); 3.92 (s, 3H); 2.96 (t, J=7.5 Hz, 2H); 2.88 (t, J=7.4 Hz, 2H); 2.13-2.07 (m, 2H); 1.33 (d, J=6.2 Hz, 6H). Methyl 5-[(isopropoxycarbonyl)amino]indane-4-carboxylate was isolated as a by-product. LCMS calc.=300.1; found=299.9 (M+Na)+. 1H NMR (500 MHz, CDCl3) a 10.07 (s, 1H); 8.21 (d, J=8.4 Hz, 1H); 7.36 (d, J=8.4 Hz, 1H); 5.06-5.00 (m, 1H); 3.93 (s, 3H); 3.19 (t, J=7.5 Hz, 2H); 2.89 (t, J=7.5 Hz, 2H); 2.08-2.02 (m, 2H); 1.32 (d, J=6.2 Hz, 6H).

후처리

  1. customthe organic layer was separated
  2. extractionThe aqueous layer was extracted with CH2Cl2 (2×)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (Si, hexanes/EtOAc)

출처 및 근거

ORD 기록
ord-e46b960c9f88460bbed32ed96bb00d44
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910592B2

반응 노트

불러오는 중…