Isopropylamine → HCID 117599990, compound

HRID 513227Notes

Reaction equation

HRID 513227 reaction equation
C(O[C:4](=[O:20])[C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:6]=1[C:12](=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)C.[CH:21]([NH2:24])([CH3:23])[CH3:22].C([BH3-])#N.[Na+]>C(Cl)CCl.CO.[Ti](Cl)(Cl)(Cl)Cl>[Br:11][C:8]1[CH:7]=[C:6]2[C:5](=[CH:10][CH:9]=1)[C:4](=[O:20])[N:24]([CH:21]([CH3:23])[CH3:22])[CH:12]2[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 3

HCID 6363IsopropylamineHCID 5003444Sodium cyanoborohydride2×HCID 117599862HCID 117599862, compound

Product 1

HCID 117599990HCID 117599990, compound

Reagents, catalysts & solvents 3

HCID 24193Titanium TetrachlorideCatalystHCID 111,2-DichloroethaneSolventHCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

2-Benzoyl-4-bromo-benzoic acid ethyl ester (50 mg; 0.15 mmol) is dissolved in ethylene dichloride (1 ml) and treated with 1 mol/l Titanium(IV)chloride solution (150 μl; 0.15 mmol) and cooled down to 0° C. Isopropylamine (13 μl; 0.15 mmol) is added and stirred for 2 hours at ambient temperature and 16 hours at 80° C. A 6.5 mol/l solution of sodium cyano borohydride in methanol (140 μl; 0.90 mmol) is added and stirred for 3 days followed by another portion of sodium cyano borohydride in methanol and 16 hours at 50° C.

Workup

  1. stirringstirred for 3 days

Sources & evidence

ORD record
ord-f91875708f864b529407e8854aed9b9b
Source dataset
uspto-grants-2015_08
Patent number
US09102684B2

Reaction notes

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