Formaldehyde → HCID 86700927, compound

HRID 1844856Notes

Reaction equation

HRID 1844856 reaction equation
N[C@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][CH2:10][CH2:11][CH2:12][CH3:13])=[O:8])[CH2:3]1.[CH2:14]=O.S([O-])([O-])(=O)=O.[Mg+2].[C:22]([BH3-])#[N:23].[Na+]>O.C(O)(=O)C.CO>[CH3:14][N:23]([CH3:22])[C@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][CH2:10][CH2:11][CH2:12][CH3:13])=[O:8])[CH2:3]1

Participants

8

Reactant 4

HCID 712FormaldehydeHCID 24083Sulfuric acid magnesium salt (1:1)HCID 5003444Sodium cyanoborohydrideHCID 67531081HCID 67531081, compound

Product 1

HCID 86700927HCID 86700927, compoundYield 186.7%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a dried 100 mL single-mouth round bottom flask were added absolute methanol (40 mL), and then the starting materials (S)-butyl 3-aminopyrrolidine-1-carboxylate (1.86 g, 10 mmol), paraformaldehyde (3 g), anhydrous magnesium sulfate (2.5 g), acetic acid (1.2 g) and sodium cyanoborohydride (2.5 g, 39.8 mmol). The mixture was stirred at room temperature for 24 hr. The reaction system was poured into water to quench, concentrated under reduced pressure. The residue was extracted with ethyl acetate, the combined organic layer was concentrated under reduced pressure to obtain a crude yellow viscous product (4.0 g).

Workup

  1. customto quench
  2. concentrationconcentrated under reduced pressure
  3. extractionThe residue was extracted with ethyl acetate
  4. concentrationthe combined organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c12477ec40a3481d8001abee45096a51
Source dataset
uspto-grants-2015_02
Patent number
US08946279B2

Reaction notes

Loading…