Phenylacetaldehyde → HCID 21904393, compound

HRID 1246909Notes

Reaction equation

HRID 1246909 reaction equation
[C:1]1([CH2:7][CH:8]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(OC([N:20]1[CH2:29][CH2:28][C:23]2([O:27][CH2:26][CH2:25][O:24]2)[CH:22]([CH2:30][CH:31]([CH3:41])[C:32]([NH:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[O:33])[CH2:21]1)=O)C1C=CC=CC=1>CO.[Pd]>[CH2:8]([N:20]1[CH2:29][CH2:28][C:23]2([O:24][CH2:25][CH2:26][O:27]2)[CH:22]([CH2:30][CH:31]([CH3:41])[C:32]([NH:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)=[O:33])[CH2:21]1)[CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 998PhenylacetaldehydeHCID 69593428HCID 69593428, compound

Product 1

HCID 21904393HCID 21904393, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Phenylacetaldehyde (0.87 mL, 7.40 mmol) was added to a solution of (8-benzyloxycarbonyl-1,4-dioxa-8-aza-spiro[4.5]-decane-6-ylmethyl)-N-phenylpropionamide (96) in MeOH (49.4 mL, 0.03M) in a hydrogenation flask. 20% Pd/C (0.53 g) was added, and the mixture was shaken under 40 psi H2 until the consumption of H2 ceased and the reaction was judged complete by TLC (3.5 h). The crude reaction mixture was passed through a column of Celite, concentrated in vacuo, and purified by flash column chromatography (60:38:2::Hexanes:CH2Cl2:2N NH3 in EtOH) to obtain pure (8-phenethyl-1,4-dioxa-8-aza-spiro[4.5]-decane-6-ylmethyl)-N-phenylpropionamide (97) (0.59 g, 92%). 1H NMR (CDCl3): 7.42–7.12 (10H, m), 4.08 (1H, dd, J=13.4, 9.5 Hz), 3.96–3.77 (4H, m), 3.65 (1H, broad d, J=10.9 Hz), 2.92–2.80 (1H, m), 2.80–2.64 (3H, m), 2.64–2.51 (2H, m), 2.33 (2H, broad t, J=10.3 Hz) 2.20–1.94 (3H, m), 1.72 (1H, dt, J=13.3, 13.2, 3.7 Hz), 1.58 (1H, ddd, J=13.1, 10.9, 4.3 Hz), 1.03 (3H, t, J=7.4 Hz) ppm. LRMS: 408.86.

Workup

  1. customwas judged complete by TLC (3.5 h)
  2. customThe crude reaction mixture
  3. concentrationconcentrated in vacuo
  4. custompurified by flash column chromatography (60:38:2::Hexanes:CH2Cl2:2N NH3 in EtOH)

Sources & evidence

ORD record
ord-bf229d81b7ef44109bd03a51e4fab581
Source dataset
uspto-grants-2006_10
Patent number
US07129228B2

Reaction notes

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