Acetone → tert-Butyl {1-[5-chloro-3-(1-isopropylazetidin-3-yl)-2-methoxy-4-methylphenyl]ethyl}carbamate

HRID 510937Notes

Reaction equation

HRID 510937 reaction equation
[NH:1]1[CH2:4][CH:3]([C:5]2[C:6]([O:23][CH3:24])=[C:7]([CH:13]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH3:14])[CH:8]=[C:9]([Cl:12])[C:10]=2[CH3:11])[CH2:2]1.CO.[CH3:27][C:28]([CH3:30])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(#N)C.O.C1COCC1>[Cl:12][C:9]1[C:10]([CH3:11])=[C:5]([CH:3]2[CH2:4][N:1]([CH:28]([CH3:30])[CH3:27])[CH2:2]2)[C:6]([O:23][CH3:24])=[C:7]([CH:13]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH3:14])[CH:8]=1

Participants

8

Reactant 4

HCID 180AcetoneHCID 887MethanolHCID 5049666Sodium triacetoxyborohydrideHCID 131733267tert-Butyl [1-(3-azetidin-3-yl-5-chloro-2-methoxy-4-methylphenyl)ethyl]carbamate

Product 1

HCID 86666855tert-Butyl {1-[5-chloro-3-(1-isopropylazetidin-3-yl)-2-methoxy-4-methylphenyl]ethyl}carbamate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of tert-butyl [1-(3-azetidin-3-yl-5-chloro-2-methoxy-4-methylphenyl)ethyl]carbamate (20 mg, 0.06 mmol) in acetonitrile (0.2 mL)/methanol (0.2 mL)/THF (0.2 mL) was added acetone (48 μL, 0.65 mmol). The mixture was stirred at room temperature for 30 min before the addition of sodium triacetoxyborohydride (36 mg, 0.17 mmol). The mixture was stirred at room temperature for 4 hours. The mixture was then diluted with water and extracted with dichloromethane. The organic layers were dried over MgSO4 and concentrated to give the crude product. LCMS calculated for C21H34ClN2O3 (M+H)+: m/z=397.2. found: 397.2.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic layers were dried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c7e725ac99c04aa3a5a78f949668960c
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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