Acetic Acid → HCID 66661375, compound

HRID 1664722Notes

Reaction equation

HRID 1664722 reaction equation
[CH2:1]1[C:6]2([CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[CH2:5][CH2:4][N:3]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:2]1.[CH:19](=O)[CH2:20][CH2:21][CH3:22].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.O>[CH2:19]([N:9]1[CH2:10][CH2:11][C:6]2([CH2:1][CH2:2][N:3]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:4][CH2:5]2)[CH2:7][CH2:8]1)[CH2:20][CH2:21][CH3:22]

Participants

7

Reactant 4

HCID 176Acetic Acid2×HCID 261Butanal2×HCID 5049666Sodium triacetoxyborohydride2×HCID 15296367tert-Butyl 3,9-diazaspiro[5.5]undecane-3-carboxylate

Product 1

HCID 66661375HCID 66661375, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 3,9-diazaspiro[5.5]undecane-3-carboxylate (150 mg, 0.59 mmol) was dissolved in 10 ml of absolute dichloromethane and admixed with butyraldehyde (52 μl, 1 eq.). With ice bath cooling, 17 μl of glacial acetic acid (0.5 eq.) and sodium triacetoxyborohydride (137 mg, 1.1 eq.) were added. The mixture was stirred at RT for 16 h. Owing to incomplete reaction, butyraldehyde (52 μl, 1 eq.), glacial acetic acid (17 μl, 0.5 eq.) and sodium triacetoxyborohydride (137 mg, 1.1 eq.) were again added. After stirring at RT for a further 4 h, a little water was added and the reaction mixture was washed with saturated NH4Cl solution. The organic phase was dried over MgSO4 and freed from the solvent under reduced pressure. The product was obtained as a colorless oil.

Workup

  1. temperatureWith ice bath cooling
  2. additionwere again added
  3. stirringAfter stirring at RT for a further 4 h
  4. washthe reaction mixture was washed with saturated NH4Cl solution
  5. dry with materialThe organic phase was dried over MgSO4
  6. customThe product was obtained as a colorless oil

Sources & evidence

ORD record
ord-1bd82dacf7414f2b98fe81f01a12a642
Source dataset
uspto-grants-2011_10
Patent number
US08039480B2

Reaction notes

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