Aminoacetaldehyde dimethyl acetal → HCID 59006342, compound

HRID 2378934Notes

Reaction equation

HRID 2378934 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[CH3:15][O:16][CH:17]([O:20][CH3:21])[CH2:18][NH2:19].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH3:15][O:16][CH:17]([O:20][CH3:21])[CH2:18][NH:19][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 89728Aminoacetaldehyde dimethyl acetalHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride2×

Product 1

HCID 59006342HCID 59006342, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

tert-Butyl 4-oxopiperidine-1-carboxylate (10.56 g, 53.0 mmol) was dissolved in 1,2-dichloroethane (100 ml). 4 Å Molecular sieves were added to the mixture followed by aminoacetaldehyde dimethyl acetal (8.0 ml, 73.4 mmol). Mixture was heated to reflux and held with stirring for 2 hours. Mixture was cooled to room temperature. Sodium triacetoxyborohydride (12.05 g, 56.9 mmol) was added to the mixture. Reaction stirred at room temperature for 3 hours. Another 3.22 g of sodium triacetoxyborohydride was added to the mixture. Reaction stirred at room temperature for 17 hours. Mixture was filtered over celite. Solids were washed with 50 mL dichloromethane. Material was extracted from the filtrate 3 times with 1N hydrochloric acid and the organic phase was discarded. Aqueous phase was made basic with sodium carbonate. Material was extracted three times with dichloromethane and the aqueous phase was discarded. Organics were dried MgSO4, filtered and then concentrated to dryness. Title compound was obtained as amber oil in 74% yield. MS (M+H)+=289.1.

Workup

  1. addition4 Å Molecular sieves were added to the mixture
  2. temperatureMixture was heated
  3. temperatureto reflux
  4. customReaction
  5. stirringstirred at room temperature for 3 hours
  6. customReaction
  7. stirringstirred at room temperature for 17 hours
  8. filtrationMixture was filtered over celite
  9. washSolids were washed with 50 mL dichloromethane
  10. extractionMaterial was extracted from the filtrate 3 times with 1N hydrochloric acid
  11. extractionMaterial was extracted three times with dichloromethane
  12. filtrationfiltered
  13. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-39604928c82e4b9586f4c6131ac06c3a
Source dataset
uspto-grants-2008_12
Patent number
US07470680B2

Reaction notes

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