Acetic Acid → 1104193-66-9

HRID 1669399Notes

Reaction equation

HRID 1669399 reaction equation
[CH:1]1([CH:4]=O)[CH2:3][CH2:2]1.[CH3:6][O:7][CH:8]([O:11][CH3:12])[CH2:9][NH2:10].[BH3-]C#N.[Na+].CC(O)=O>CO>[CH:1]1([CH2:4][NH:10][CH2:9][CH:8]([O:11][CH3:12])[O:7][CH3:6])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 89728Aminoacetaldehyde dimethyl acetalHCID 123114CyclopropanecarboxaldehydeHCID 5003444Sodium cyanoborohydride

Product 1

HCID 457925181104193-66-9Yield 61%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of cyclopropanecarboxaldehyde in MeOH (0.2 M) was treated with 2,2-dimethoxyethylamine (1.2 eq). The solution was cooled with an ice/water bath and treated portionwise with NaCNBH3 (1.0 eq). The pH of the resulting solution was adjusted to 6 with AcOH, and the reaction left at RT for 24 h. The mixture was concentrated, diluted with EtOAc, washed with sat. aq. NaHCO3, brine, dried (Na2SO4), filtered and concentrated in vacuo to afford the product (61%). 1H NMR (300 MHz, DMSO-d6, 300 K) δ 0.05-0.07 (m, 2H), 0.15-0.17 (m, 2H), 0.87-0.93 (m, 1H), 2.39-2.41 (m, 2H), 2.64-2.66 (m, 2H), 3.3 (s, 6H), 4.46 (t, J 3.0, 1H), 5.38 (m, 1H).

Workup

  1. temperatureThe solution was cooled with an ice/water bath
  2. concentrationThe mixture was concentrated
  3. additiondiluted with EtOAc
  4. washwashed with sat. aq. NaHCO3, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1d5e3ed242bc461888c6fe55e2a6cd85
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Reaction notes

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