Formaldehyde → HCID 20803296, compound

HRID 1670020Notes

Reaction equation

HRID 1670020 reaction equation
[CH3:1][O:2][C:3](=[O:9])[C@H:4]1[CH2:8][CH2:7][CH2:6][NH:5]1.[CH2:10]=O>CN(C=O)C>[CH3:1][O:2][C:3](=[O:9])[C@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[CH3:10]

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 853476D-Proline methyl ester

Product 1

HCID 20803296HCID 20803296, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(2R)-proline methylester (1.20 g, 10.0 mmol) was dissolve in DMF (30 mL), and formalin (37% in water, 1.12 mL, 15.0 mmol) and NaBH (OAc)3 (4.20 g, 20.0 mmol) were added portionwise. After 12 h, the reaction material was concentrated in vacuo, and the residue was diluted with NaHCO3 (30 mL). The organic material was extracted with EtOAc, and the organic extracts were dried over MgSO4 and concentrated in vacuo. The residue was purified by column chomatography (EtOAc/Hex=4/1) to give the title compound (1.33 g, 93.0%).

Workup

  1. concentrationthe reaction material was concentrated in vacuo
  2. additionthe residue was diluted with NaHCO3 (30 mL)
  3. extractionThe organic material was extracted with EtOAc
  4. dry with materialthe organic extracts were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chomatography (EtOAc/Hex=4/1)

Sources & evidence

ORD record
ord-eb3a8e91ebaa468084ee19832f0d7f82
Source dataset
uspto-grants-2011_08
Patent number
US07989634B2

Reaction notes

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