Acetic Acid → HCID 67460442, compound

HRID 554868Notes

Reaction equation

HRID 554868 reaction equation
[Br:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH:7]2[CH2:10][NH:9][CH2:8]2)=[C:4]([O:13][CH3:14])[CH:3]=1.[C:15]1(=O)[CH2:18][CH2:17][CH2:16]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClC(Cl)C>[Br:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH:7]2[CH2:10][N:9]([CH:15]3[CH2:18][CH2:17][CH2:16]3)[CH2:8]2)=[C:4]([O:13][CH3:14])[CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14496CyclobutanoneHCID 5049666Sodium triacetoxyborohydrideHCID 67461149HCID 67461149, compound

Product 1

HCID 67460442HCID 67460442, compoundYield 56.6%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Dissolve 3-(4-bromo-2-methoxy-phenoxy)-azetidine (1.84 g, 7.13 mmol) in dichloroethane (80 mL). Add cyclobutanone (1.86 mL, 25 mmol), sodium triacetoxyborohydride (3.02 g, 14.3 mmol) and acetic acid (0.82 mL, 14.3 mmol). Stir the mixture overnight, then add saturated sodium bicarbonate and extract three times using dichloromethane. Dry the combined organic portions over sodium sulfate, filter, and concentrate. Purify by silica gel chromatography using a 0-3% gradient of methanol/dichloromethane to give 1.26 g (56%) of the title compound.

Workup

  1. extractionadd saturated sodium bicarbonate and extract three times
  2. dry with materialDry the combined organic portions over sodium sulfate
  3. filtrationfilter
  4. concentrationconcentrate
  5. customPurify by silica gel chromatography

Sources & evidence

ORD record
ord-030715f0200f453bbd869e370370bce2
Source dataset
uspto-grants-2011_11
Patent number
US08049013B2

Reaction notes

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