Methyl 2-formylbenzoate → HCID 66601480, compound

HRID 409887Notes

Reaction equation

HRID 409887 reaction equation
[C:1]([N:8]1[CH2:11][CH:10]([NH2:12])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH:13]([C:15]1[CH:24]=[CH:23][CH:22]=[CH:21][C:16]=1[C:17](OC)=O)=[O:14].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl.C(O)(=O)C>[O:14]=[C:13]1[C:15]2[C:16](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:17][N:12]1[CH:10]1[CH2:11][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9]1

Participants

6

Reactant 3

HCID 243003Methyl 2-formylbenzoateHCID 1516507Tert-butyl 3-aminoazetidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 66601480HCID 66601480, compoundYield 87.3%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolvent

Procedure

To a solution of 1-Boc-3-aminoazetidine 1a (1.0 g, 5.8 mmol) and methyl 2-formylbenzoate 2a (0.95 g, 5.8 mmol) in 1,2-dichloroethane (30 mL) and acetic acid (1.5 mL) was added Na(OAc)3BH (1.29 g, 6.08 mmol) at room temperature. The reaction was stirred for 5.5 h. It was quenched with aq. NaHCO3, and the resulting mixture was extracted with CH2Cl2. The organic solution was dried over Na2SO4 and concentrated. Purification by flash column chromatography (silica gel, 40% EtOAc/heptane) gave compound 2b (1.46 g).

Workup

  1. customIt was quenched with aq. NaHCO3
  2. extractionthe resulting mixture was extracted with CH2Cl2
  3. dry with materialThe organic solution was dried over Na2SO4
  4. concentrationconcentrated
  5. customPurification by flash column chromatography (silica gel, 40% EtOAc/heptane)

Sources & evidence

ORD record
ord-c08899423d6844d49c87bbc52d58571b
Source dataset
uspto-grants-2014_06
Patent number
US08759533B2

Reaction notes

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