Acetic Acid → HCID 18770462, compound

HRID 479390Notes

Reaction equation

HRID 479390 reaction equation
C([BH3-])#N.[Na+].[C:5]([O:9][C:10]([N:12]1[CH2:17][CH2:16][CH:15]([CH2:18][NH2:19])[CH2:14][CH2:13]1)=[O:11])([CH3:8])([CH3:7])[CH3:6].[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][CH:30]([CH:33]=O)[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21].C(O)(=O)C>CO>[C:5]([O:9][C:10]([N:12]1[CH2:17][CH2:16][CH:15]([CH2:18][NH:19][CH2:33][CH:30]2[CH2:31][CH2:32][N:27]([C:25]([O:24][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:26])[CH2:28][CH2:29]2)[CH2:14][CH2:13]1)=[O:11])([CH3:8])([CH3:7])[CH3:6]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7368171-Boc-4-(aminomethyl)piperidineHCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 18770462HCID 18770462, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Sodium cyanoborohydride (440 mg; 7.0 mmol) was added to a solution of [(1-tert-butoxycarbonyl-4-piperidinyl)-methyl]amine (1.5 g; 7.0 mmol) in methanol (30 ml) under ice cooling, and the mixture was stirred for 15 minutes. A solution of 1-tert-butoxycarbonyl-4-piperidine-carbaldehyde (1.4 g; 9.1 mmol) in methanol (5 ml) and acetic acid (0.40 ml; 7.0 mmol) were added to the resultant solution, and the mixture was stirred for 4 hours. After the ice bath was removed, the mixture was stirred at room temperature for 48 hours. The reaction mixture was concentrated under reduced pressure and the resultant concentrated residue was added to a saturated aqueous solution of sodium hydrogencarbonate to conduct extraction with chloroform. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resultant crude oil was purified by column chromatography on silica gel, thereby obtaining 1.83 g (yield: 63%) of N,N-bis[(1-tert-butoxycarbonyl-4-piperidinyl)methyl]amine as a colorless oil.

Workup

  1. stirringthe mixture was stirred for 4 hours
  2. customAfter the ice bath was removed
  3. stirringthe mixture was stirred at room temperature for 48 hours
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. additionthe resultant concentrated residue was added to a saturated aqueous solution of sodium hydrogencarbonate
  6. extractionextraction with chloroform
  7. washThe organic layer was washed with saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe resultant crude oil was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-af35f2c2180640d6b38c5a6e332fb664
Source dataset
uspto-grants-2003_11
Patent number
US06645957B2

Reaction notes

Loading…