(Phenylmethoxy)acetaldehyde → HCID 11775292, compound

HRID 1983438Notes

Reaction equation

HRID 1983438 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:13](Cl)(Cl)[C:14]([OH:16])=[O:15].[CH2:19]([C@@H]1N[C@H](C(C)(C)C)N(C)C1=O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(OCC)C>[CH2:1]([O:8][C@@H:13]1[C@@H:10]([OH:11])[C@H:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C@@H:9]([CH2:10][O:11][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[O:16][CH:14]1[OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 108989(Phenylmethoxy)acetaldehydeHCID 10309833HCID 10309833, compound

Product 1

HCID 11775292HCID 11775292, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Freshly distilled benzyloxyacetaldehyde (150 mg, 1.0 mmol) was added to a stirring solution of (2S,5S)-5-benzyl-2-tert-butyl-3-methylimidazolidin-4-one trichloroacetate (27.3 mg, 67 mmol) in diethyl ether (330 μL, 3.0 M) at −20° C. After complete consumption of the starting material was determined by TLC analysis (24 h), the reaction mixture was diluted with ethyl acetate, washed with saturated NH4Cl, brine, dried over anhydrous Na2SO4 and concentrated in vacuo. Flash chromatography (19:1 dichloromethane:diethyl ether) afforded the title compound as a clear, colorless oil in 85% yield (104 mg, 0.69 mmol), 95% ee, and 11:1 dr. 1H NMR (300 MHz, CDCl3) δ 7.31 (m, 15H, Ar—H), 5.38 (m, 1H, OCHO), 4.83 (m, 1H, CHCH2), 4.55 (br, m, 5H), 4.12 (br m, 1H, 3.64 (br m, 4H, CHO), 3.30 (m, 1H, CHO); 13C NMR (75 MHz, CDCl3) δ (α-anomer) 90.4 (C-1), 74.6 (C-3), and 68.9 (C-6); (β-anomer) 97.3 (C-1), 76.9 (C-3), 69.2 (C-6), which is consistent with previously reported values (Ito et al. (1980) Carbohydrate Res. 86:193).

Workup

  1. customAfter complete consumption of the starting material
  2. customwas determined by TLC analysis (24 h)
  3. additionthe reaction mixture was diluted with ethyl acetate
  4. washwashed with saturated NH4Cl, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0ad4daf9cc2c4128a6bb395981c7c99e
Source dataset
uspto-grants-2009_06
Patent number
US07541456B2

Reaction notes

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