Acetic Acid → HCID 58504078, compound

HRID 2407828Notes

Reaction equation

HRID 2407828 reaction equation
[O:1]([C:8]1[C:13]2[C:14]([NH2:17])=[N:15][NH:16][C:12]=2[CH:11]=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:18]([CH:20]1[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]1)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>C1(C)C=CC=CC=1>[O:1]([C:8]1[C:13]2[C:14]([NH:17][CH2:18][CH:20]3[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:30])([CH3:32])[CH3:31])=[O:27])[CH2:22][CH2:21]3)=[N:15][NH:16][C:12]=2[CH:11]=[CH:10][N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 11615525HCID 11615525, compound

Product 1

HCID 58504078HCID 58504078, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of the compound prepared in Example 434 (0.217 g,) in toluene (12 mL) was added tert-butyl 4-formylpiperidine-1-carboxylate (0.205 g). The mixture was evaporated in vacuo to remove water from imine formed. Sodium triacetoxyborohydride (0.244 g) was added, followed by acetic acid (0.4 mL). After stirring at room temperature for 1 hour, the reaction mixture was quenched with methanol slowly, to decompose excess borohydride, and then concentrated in vacuo. Ethyl acetate, was added to the residue and then washed with aqueous saturated sodium bicarbonate, dried, evaporated in vacuo to provide the title compound (0.262 g) with the following physical data.

Workup

  1. customThe mixture was evaporated in vacuo
  2. customto remove water from imine
  3. customformed
  4. customthe reaction mixture was quenched with methanol slowly
  5. concentrationconcentrated in vacuo
  6. additionEthyl acetate, was added to the residue
  7. washwashed with aqueous saturated sodium bicarbonate
  8. customdried
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-196501bd233b48269a043ef82c051583
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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