Acetic Acid → N-[1-(3-Chlorobenzyl)-6-cyano-1,2,3,4-tetrahydroquinolin-3-yl]-carbamic acid tert-butyl ester

HRID 2234248Notes

Reaction equation

HRID 2234248 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][CH:8]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:18]#[N:19])[CH:15]=2)[NH:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[Cl:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH:25]=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(O)(=O)C>ClCCCl>[C:1]([O:5][C:6](=[O:20])[NH:7][CH:8]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:18]#[N:19])[CH:15]=2)[N:10]([CH2:25][C:24]2[CH:27]=[CH:28][CH:29]=[C:22]([Cl:21])[CH:23]=2)[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 114773-ChlorobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 66692977tert-Butyl (6-cyano-1,2,3,4-tetrahydroquinolin-3-yl)carbamate

Product 1

HCID 68581117N-[1-(3-Chlorobenzyl)-6-cyano-1,2,3,4-tetrahydroquinolin-3-yl]-carbamic acid tert-butyl esterYield 48%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of (6-cyano-1,2,3,4-tetrahydroquinolin-3-yl)-carbamic acid tert-butyl ester (820 mg, 3 mmol), prepared as described in Example 1C, and 3-chloro benzaldehyde (0.34 mL, 3 mmol) in DCE (10 mL) was added NaBH(OAc)3 (1.78 g, 8.4 mmol), followed by acetic acid (0-34 mL, 6 mmol). The reaction was stirred at RT for 16 h, then quenched with saturated aqueous NaHCO3, extracted with CH2Cl2 (30 mL×3). The organic extracts were washed with water, saturated aqueous NaCl, dried (Na2SO4), and concentrated. The resulting residue was chromatographed (silica gel) eluting with EtOAc (10-50%) in hexanes to give the title compound (571 mg, 48%) as a foam.

Workup

  1. customquenched with saturated aqueous NaHCO3
  2. extractionextracted with CH2Cl2 (30 mL×3)
  3. washThe organic extracts were washed with water, saturated aqueous NaCl
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe resulting residue was chromatographed (silica gel)
  7. washeluting with EtOAc (10-50%) in hexanes

Sources & evidence

ORD record
ord-59f0318a899f435eb20723a2fe7ee0c4
Source dataset
uspto-grants-2010_05
Patent number
US07709647B2

Reaction notes

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