3-(Trifluoromethyl)benzaldehyde → tert-Butyl [1-[[3-(trifluoromethyl)phenyl]methyl]azetidin-3-yl]carbamate

HRID 1667219Notes

Reaction equation

HRID 1667219 reaction equation
[NH:1]1[CH2:4][CH:3]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH2:2]1.[F:13][C:14]([F:24])([F:23])[C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.ClCCl>[F:13][C:14]([F:23])([F:24])[C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH2:18][N:1]1[CH2:4][CH:3]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:9])([CH3:11])[CH3:10])[CH2:2]1

Participants

6

Reactant 3

HCID 679903-(Trifluoromethyl)benzaldehydeHCID 15194053-Aminoazetidine, 3-BOC protectedHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 67445744tert-Butyl [1-[[3-(trifluoromethyl)phenyl]methyl]azetidin-3-yl]carbamate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of tert-butyl azetidin-3-ylcarbamate (0.34 g, 2 mmol) in dichloroethane was added 3-(trifluoromethyl)benzaldehyde (0.45 g, 2.6 mmol) and sodium triacetoxyborohydride (0.64 g, 3 mmol). The resultant mixture was stirred at room temperature for 16 hours, and then the mixture was diluted with dichloromethane and washed with aqueous NaHCO3 solution. The organic layer was separated, dried over MgSO4, and concentrated. The residue was purified by flash chromatography on silica gel eluting with 30-70% ethyl acetate/hexane to yield the title compound.

Workup

  1. washwashed with aqueous NaHCO3 solution
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography on silica gel eluting with 30-70% ethyl acetate/hexane

Sources & evidence

ORD record
ord-99b53b3be0104ec38d93e2a522af8ae2
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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