Acetic Acid → HCID 67051794, compound

HRID 1809005Notes

Reaction equation

HRID 1809005 reaction equation
[CH3:1][C@@H:2]1[C:6]2([CH2:9][NH:8][CH2:7]2)[O:5][C:4](=[O:10])[NH:3]1.C(O)(=O)C.[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([BH3-])#N.[Na+].Cl>CO>[CH3:1][C@@H:2]1[C:6]2([CH2:9][N:8]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:7]2)[O:5][C:4](=[O:10])[NH:3]1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 55288477HCID 55288477, compound

Product 1

HCID 67051794HCID 67051794, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of (8R)-8-methyl-5-oxa-2,7-diazaspiro[3.4]octan-6-one (937 mg, 6.6 mmol), acetic acid (0.756 mL, 13.2 mmol), and benzaldehyde (1.0 mL, 9.9 mmol) in methanol (65 mL) was treated with sodium cyanoborohydride (829 mg, 13.2 mmol) at rt for min. The mixture was then cooled to 0° C., and 3 N hydrochloric acid (100 mL) was added. The methanol was then removed in vacuo. The resulting aqueous solution was washed with ethyl acetate. The ethyl acetate wash was back extracted with 1 N hydrochloric acid, and the aqueous acidic phases were combined and basified with potassium carbonate. The organic phase was discarded. The aqueous mixture was then extracted three times with ethyl acetate. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated in vacuo. The desired (8R)-8-methyl-2-(phenylmethyl)-5-oxa-2,7-diazaspiro[3.4]octan-6-one was obtained in 93% purity as a milky colorless liquid (1.33 g, 5.73 mmol, 87% yield). MS (EI) for C13H16N2O2: 233 (MH+).

Workup

  1. customThe methanol was then removed in vacuo
  2. washThe resulting aqueous solution was washed with ethyl acetate
  3. washThe ethyl acetate wash
  4. extractionwas back extracted with 1 N hydrochloric acid
  5. extractionThe aqueous mixture was then extracted three times with ethyl acetate
  6. dry with materialThe combined organic extracts were dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6fb366d33be245b7be4f4f6c6dbe957b
Source dataset
uspto-grants-2013_01
Patent number
US08362002B2

Reaction notes

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