Acetic Acid → (1-Benzyl-6-bromo-1,2,3,4-tetrahydroquinolin-3-yl)-carbamic acid tert-butyl ester

HRID 2234252노트

반응식

HRID 2234252 반응식
[C:1]([O:5][C:6](=[O:19])[NH:7][CH:8]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Br:18])[CH:15]=2)[NH:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH:20](=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CC(O)=O>ClCCCl>[C:1]([O:5][C:6](=[O:19])[NH:7][CH:8]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Br:18])[CH:15]=2)[N:10]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 17758659tert-Butyl (6-bromo-1,2,3,4-tetrahydroquinolin-3-yl)carbamate

생성물 1

HCID 59297053(1-Benzyl-6-bromo-1,2,3,4-tetrahydroquinolin-3-yl)-carbamic acid tert-butyl ester수율 81.5%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

To a solution of (6-bromo-1,2,3,4-tetrahydroquinolin-3-yl)-carbamic acid tert-butyl ester (1.636 g, 5 mmol), prepared as described in Example 1B, in DCE (16 mL) at RT was added benzaldehyde (1 mL, 10 mmol), followed by NaBH(OAc)3 (2.97 g, 14 mmol) and AcOH (0.6 mL, 10 mmol). The reaction mixture was stirred at RT for 16 h, then quenched with aqueous NaHCO3 (40 mL) and extracted with CH2Cl2 (50 mL×3). The combined extracts were washed with saturated aqueous NaCl, dried (Na2SO4), and concentrated. The resulting residue was chromatographed (silica gel) eluting with 0-20% of EtOAc in hexanes to give the title compound (1.70 g, 81%) as a white foam.

후처리

  1. customquenched with aqueous NaHCO3 (40 mL)
  2. extractionextracted with CH2Cl2 (50 mL×3)
  3. washThe combined extracts were washed with saturated aqueous NaCl
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe resulting residue was chromatographed (silica gel)
  7. washeluting with 0-20% of EtOAc in hexanes

출처 및 근거

ORD 기록
ord-2e3b1f869535469a912f28e42773e186
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07709647B2

반응 노트

불러오는 중…