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

HRID 1363091ノート

反応式

HRID 1363091 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

To a solution of 1B (1.636 g, 5 mmol) in DCE (16 mL) at RT was added benzaldehyde (1 mL, 10 mmol), followed by NaB(OAc)3H (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 brine, dried (Na2SO4), and concentrated. The resulting residue was chromatographed (silica gel) eluting with 0-20% of EtOAc in hexane to give the title compound (1.70 g, 81%) as a white foam.

後処理

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

出典と根拠

ORDレコード
ord-72f2b92f685d46e79c84aea8c8bc7dfa
出典データセット
uspto-grants-2011_02
特許番号
US07884113B2

反応ノート

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