2,2-Diethoxyethylamine → HCID 58168483, compound

HRID 446417Notes

Reaction equation

HRID 446417 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH2:15]([O:17][CH:18]([O:21][CH2:22][CH3:23])[CH2:19][NH2:20])[CH3:16].[O:24]1[CH2:29][CH2:28][C:27](=O)[CH2:26][CH2:25]1.C(=O)(O)[O-].[Na+]>ClCCl.O>[CH2:15]([O:17][CH:18]([O:21][CH2:22][CH3:23])[CH2:19][NH:20][CH:27]1[CH2:28][CH2:29][O:24][CH2:25][CH2:26]1)[CH3:16]

Participants

7

Reactant 4

HCID 695242,2-DiethoxyethylamineHCID 121599Tetrahydro-4H-pyran-4-oneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 58168483HCID 58168483, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Sodium triacetoxyborohydride (10.6 g) was added to a cooled (0° C.) solution of aminoacetaldehyde diethyl acetal (5.8 mL) and tetrahydro-4H-pyran-4-one (3.7 mL) in dichloromethane (100 mL). The reaction was stirred for 18 h, allowing the temperature to warm to ambient conditions. Water (100 mL) was added, followed by portionwise addition of sodium bicarbonate (16.8 g), causing effervescence. The mixture was stirred vigorously for 1 h, and then allowed to partition. The phases were then separated and the aqueous phase extracted with more dichloromethane (50 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo to afford the titled compound as a colourless oil. Yield 8.3 g.

Workup

  1. temperatureto warm to ambient conditions
  2. stirringThe mixture was stirred vigorously for 1 h
  3. customto partition
  4. customThe phases were then separated
  5. extractionthe aqueous phase extracted with more dichloromethane (50 mL)
  6. dry with materialThe combined organic extracts were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8a2e6958d1614f8daf06d2319d8ca6cf
Source dataset
uspto-grants-2013_07
Patent number
US08476265B2

Reaction notes

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