Formaldehyde → HCID 86700928, compound

HRID 1844858Notes

Reaction equation

HRID 1844858 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 86700929HCID 86700929, compound

Product 1

HCID 86700928HCID 86700928, compoundYield 1,773.2%

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), (R)-butyl 3-aminopyrrolidine-1-carboxylate (1.86 g, 1.0 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, The solution was concentrated under reduced pressure and the residue was extracted with ethyl acetate. The combined organ layer was dried, and was concentrated under reduced pressure to obtain a crude yellow viscous product (3.8 g).

Workup

  1. customto quench
  2. concentrationThe solution was concentrated under reduced pressure
  3. extractionthe residue was extracted with ethyl acetate
  4. customThe combined organ layer was dried
  5. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-cb86e1192081429ea2b6be8007383c3d
Source dataset
uspto-grants-2015_02
Patent number
US08946279B2

Reaction notes

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