Formaldehyde → HCID 58522509, compound

HRID 81351Notes

Reaction equation

HRID 81351 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][C@@H:8]1[CH2:13][CH2:12][NH:11][CH2:10][C@H:9]1[O:14][CH3:15])([CH3:4])([CH3:3])[CH3:2].C=O.[BH-](OC(C)=O)(OC(C)=O)O[C:21](C)=O.[Na+].C([O-])(O)=O.[Na+]>CN(C=O)C.C(O)(=O)C>[C:1]([O:5][C:6](=[O:16])[NH:7][C@@H:8]1[CH2:13][CH2:12][N:11]([CH3:21])[CH2:10][C@H:9]1[O:14][CH3:15])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 58522529HCID 58522529, compound

Product 1

HCID 58522509HCID 58522509, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

Tert-butyl((3R,4R)-3-methoxy-piperidin-4-yl)-carbamate (2.88 g) is dissolved with formaldehyde (1.79 mL, 37% solution in H2O) and acetic acid (100 μL) in DMF. Then Na(OAc)3BH (12.59 g) is added. After 20 h the reaction mixture is combined with aqueous NaHCO3 solution (saturated with NaCl) and extracted 5 times with EtOAc. The combined organic phase is dried on magnesium sulphate, filtered off from the desiccant and the solvent is eliminated in vacuo. The residue is used in the next reaction step without any further purification.

Workup

  1. extractionextracted 5 times with EtOAc
  2. customThe combined organic phase is dried on magnesium sulphate
  3. filtrationfiltered off from the desiccant and the solvent
  4. customThe residue is used in the next reaction step without any further purification

Sources & evidence

ORD record
ord-01388e644aa04da893ce4dfc73f57227
Source dataset
uspto-grants-2014_09
Patent number
US08846689B2

Reaction notes

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