Acetic Acid → HCID 58006279, compound

HRID 215936Notes

Reaction equation

HRID 215936 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:3][CH2:2]1.[CH:15]([N:18]([C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH:22]=O)[CH3:19])([CH3:17])[CH3:16].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CC(O)=O>C(Cl)Cl>[CH:15]([N:18]([C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH2:22][N:1]1[CH2:2][CH2:3][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])[CH2:5][CH2:6]1)[CH3:19])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7238334-(N-Boc-amino)piperidineHCID 5049666Sodium triacetoxyborohydrideHCID 286037051021239-93-9

Product 1

HCID 58006279HCID 58006279, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl piperidin-4-ylcarbamate (262 mg, 1.31 mmol) (Aldrich) and 2-(N-isopropyl-N-methylamino)benzaldehyde (150 mg, 0.85 mmol) in CH2Cl2 (6 mL) was added Na(OAc)3BH (288 mg, 1.36 mmol) followed by AcOH (0.1 mL). This mixture was stirred for 3 h at RT. The reaction was quenched by adding 2M NaOH—H2O (5 mL) and stirred for 5 min. The mixture was then extracted with CH2Cl2 (2×25 mL), and the organic layer was washed with brine, and dried, and the solvent was removed. The crude material was purified by silica gel column chromatography eluting with 5% NH3-MeOH in CH2Cl2 gave Compound 221.

Workup

  1. customThe reaction was quenched
  2. additionby adding 2M NaOH—H2O (5 mL)
  3. stirringstirred for 5 min
  4. extractionThe mixture was then extracted with CH2Cl2 (2×25 mL)
  5. washthe organic layer was washed with brine
  6. customdried
  7. customthe solvent was removed
  8. customThe crude material was purified by silica gel column chromatography
  9. washeluting with 5% NH3-MeOH in CH2Cl2

Sources & evidence

ORD record
ord-22cb42fe181c49e9a9a36fe6daf90abb
Source dataset
uspto-grants-2012_06
Patent number
US08193203B2

Reaction notes

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