Acetic Acid → 1-tert-butyl 3-methyl (3R,5S)-5-[(2-methylpropyl)amino]piperidine-1,3-dicarboxylate

HRID 2192772Notes

Reaction equation

HRID 2192772 reaction equation
[NH2:1][C@@H:2]1[CH2:7][N:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:5][C@H:4]([C:15]([O:17][CH3:18])=[O:16])[CH2:3]1.[CH:19](=O)[CH:20]([CH3:22])[CH3:21].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[CH2:19]([NH:1][C@@H:2]1[CH2:7][N:6]([C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])[CH2:5][C@H:4]([C:15]([O:17][CH3:18])=[O:16])[CH2:3]1)[CH:20]([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6561IsobutyraldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 53677987rel-1-(tert-butyl) 3-methyl (3R,5S)-5-aminopiperidine-1,3-dicarboxylate

Product 1

HCID 593566071-tert-butyl 3-methyl (3R,5S)-5-[(2-methylpropyl)amino]piperidine-1,3-dicarboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-tert-Butyl 3-methyl (3R*,5S*)-5-aminopiperidine-1,3-dicarboxylate (370 mg) was dissolved in methanol (10 ml), isobutyraldehyde (0.137 ml), acetic acid (85 μl) and sodium triacetoxyborohydride (759 mg) were added and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure, and the concentrated solution was basified with aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the object compound (439 mg) as an oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-688ff48901ec4ac0be01471e3f0f4f68
Source dataset
uspto-grants-2012_12
Patent number
US08329691B2

Reaction notes

Loading…