Potassium Carbonate → HCID 68828627, compound

HRID 2106503Notes

Reaction equation

HRID 2106503 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.[CH2:15]([N:22]1[CH2:27][CH2:26][C:25](=O)[CH2:24][CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])([O-])=O.[K+].[K+]>C1COCC1.CC(O)=O>[C:10]([O:9][C:8](=[O:14])[NH:7][CH:4]1[CH2:3][CH2:2][N:1]([CH:25]2[CH2:24][CH2:23][N:22]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:27][CH2:26]2)[CH2:6][CH2:5]1)([CH3:11])([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 192201-Benzyl-4-piperidoneHCID 7238334-(N-Boc-amino)piperidineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 68828627HCID 68828627, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5.0 g (25.0 mmol) tert-butyl piperidin-4-yl-carbamate and 4.46 mL (25.0 mmol) 1-benzyl-piperidin-4-one in 150 mL THF was adjusted with AcOH to a pH of 5 and then combined batchwise with 5.61 g (26.5 mmol) NaBH(OAc)3 within 3 h while cooling with ice. The reaction mixture was stirred overnight at RT, then made alkaline with 500 mL 30% K2CO3 solution, stirred for 1 h at RT, extracted three times with 100 mL EtOAc and the combined organic phases were dried over Na2SO4. After elimination of the desiccant and solvent the residue was reacted further without purification.

Workup

  1. temperaturewhile cooling with ice
  2. stirringstirred for 1 h at RT
  3. extractionextracted three times with 100 mL EtOAc
  4. dry with materialthe combined organic phases were dried over Na2SO4
  5. customAfter elimination of the desiccant and solvent the residue was reacted further without purification

Sources & evidence

ORD record
ord-ee3de21d38cc4f38884efc1615295ffa
Source dataset
uspto-grants-2009_08
Patent number
US07579341B2

Reaction notes

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