Acetic Acid → tert-Butyl 1-benzyl-6-chloro-1,2,3,4-tetrahydroquinolin-3-ylcarbamate

HRID 1363087ノート

反応式

HRID 1363087 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH2:7][CH:6]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:5]2.[CH:20](=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].CC(O)=O>ClCCCl.CCOC(C)=O>[CH2:20]([N:8]1[C:9]2[C:4](=[CH:3][C:2]([Cl:1])=[CH:11][CH:10]=2)[CH2:5][CH:6]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:18])[CH3:17])[CH2:7]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

参加物

7

反応物 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 59297067tert-Butyl 6-chloro-1,2,3,4-tetrahydroquinolin-3-ylcarbamate

生成物 1

HCID 59297049tert-Butyl 1-benzyl-6-chloro-1,2,3,4-tetrahydroquinolin-3-ylcarbamate収率 80%

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 21A (310 mg, 1.096 mmol) in 1,2-dichloroethane (7 mL) was added benzaldehyde (235 mg, 2.193 mmol), followed by sodium triacetoxyborohydride (650 mg, 3.069 mmol) and AcOH (200 mg, 3.29 mmol). The reaction mixture was stirred at RT for 4 h, then diluted with EtOAc, washed with saturated aqueous NaHCO3, water, brine, dried Na2SO4) and concentrated. The resulting residue was chromatographed (silica gel) eluting with EtOAc/hexane 1:5 to give the title compound as light yellow foam (325 mg, 80%).

後処理

  1. washwashed with saturated aqueous NaHCO3, water, brine, dried Na2SO4) and
  2. concentrationconcentrated
  3. customThe resulting residue was chromatographed (silica gel)
  4. washeluting with EtOAc/hexane 1:5

出典と根拠

ORDレコード
ord-8042fda8d02d4cef93e44220a3407d03
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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