Acetic Acid → HCID 45120738, compound

HRID 1455233Notes

Reaction equation

HRID 1455233 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]=O.Cl.[NH:9]1[CH2:12][CH2:11][CH2:10]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>O1CCCC1>[N:9]1([CH2:6][C:2]2[NH:3][CH:4]=[CH:5][N:1]=2)[CH2:12][CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 249551H-imidazole-2-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 12308726Azetidine hydrochloride

Product 1

HCID 45120738HCID 45120738, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-imidazolecarboxaldehyde (3.0 g) and azetidine hydrochloride (3.21 g) in anhydrous tetrahydrofuran (180 ml) was added sodium triacetoxyborohydride (9.99 g) followed by glacial acetic acid (1.72 ml). The resultant mixture was stirred at room temperature for 22 h, after which the insoluble material was filtered and washed with ethyl acetate. The filtrate was concentrated under reduced pressure and the residue purified using silica SPE (eluting with DCM, methanol, methanol:20% aqueous ammonia) to give the title compound (2.63 g) as a beige solid.

Workup

  1. filtrationafter which the insoluble material was filtered
  2. washwashed with ethyl acetate
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue purified
  5. washsilica SPE (eluting with DCM, methanol, methanol:20% aqueous ammonia)

Sources & evidence

ORD record
ord-1aac2e76ef484db9b21b09611f1c1c91
Source dataset
uspto-grants-2009_01
Patent number
US07482374B2

Reaction notes

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