Formaldehyde → HCID 68414999, compound

HRID 220237Notes

Reaction equation

HRID 220237 reaction equation
C=O.[NH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.N1CCC[C@H:11]1C(O)=O.[C:18]1(=[O:24])[CH2:23][CH2:22][CH2:21][CH:20]=[CH:19]1>CS(C)=O>[C:4]1([N:3]2[CH2:11][C@@H:23]3[CH2:22][CH2:21][C@H:20]2[CH2:19][C:18]3=[O:24])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 6115AnilineHCID 135942-Cyclohexen-1-oneHCID 145742L-Proline

Product 1

HCID 68414999HCID 68414999, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 2.4 mL of formaldehyde (36.5% in water), 3.1 mL of aniline and 1.0 g of (S)-proline in 125 mL of DMSO was added 6.0 mL of 2-cyclohexen-1-one. The mixture was stirred for 72 h at rt, quenched with water and extracted with toluene. The organic phase was dried over anh. Na2SO4 and concentrated in vacuo. The crude product was purified by CC using EtOAc/heptane 1/5 to 1/3 to yield 1.1 g of (1S,4S)-2-phenyl-2-aza-bicyclo[2.2.2]octan-5-one a as yellow oil.

Workup

  1. customquenched with water
  2. extractionextracted with toluene
  3. dry with materialThe organic phase was dried over anh. Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by CC

Sources & evidence

ORD record
ord-b31b9a82dcfb43e1a23f15a00f9af6be
Source dataset
uspto-grants-2012_06
Patent number
US08202885B2

Reaction notes

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