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

HRID 2234250Notes

Reaction equation

HRID 2234250 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 6-chloro-1,2,3,4-tetrahydroquinolin-3-ylcarbamate (310 mg, 1.096 mmol), prepared as described in Example 19A, 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, saturated aqueous NaCl, dried Na2SO4) and concentrated. The resulting residue was chromatographed (silica gel) eluting with EtOAc/hexanes (1:5 ratio) to give the title compound as light yellow foam (325 mg, 80%).

Workup

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

Sources & evidence

ORD record
ord-48ec7594f5d64d35848421d06afb1c1a
Source dataset
uspto-grants-2010_05
Patent number
US07709647B2

Reaction notes

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