Sodium Hydroxide → HCID 86700513, compound

HRID 1500523Notes

Reaction equation

HRID 1500523 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][C@@H:10]([CH3:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:15]([O:22][C:23]([N:25]1[CH2:30][CH2:29][C:28](=O)[CH2:27][CH2:26]1)=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([BH3-])#N.[Na+].[OH-].[Na+]>CO.C(O)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:28]2[CH2:29][CH2:30][N:25]([C:23]([O:22][CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[O:24])[CH2:26][CH2:27]2)[C@@H:10]([CH3:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 643496Benzyl 4-oxopiperidine-1-carboxylateHCID 5003444Sodium cyanoborohydrideHCID 7023035(S)-1-Boc-3-methylpiperazine

Product 1

HCID 86700513HCID 86700513, compoundYield 34.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of (S)-3-methyl-piperazine-1-carboxylic acid tert-butyl ester (1.0 g, mmol) and N-benzyloxycarbonyl-4-piperidone (1.2 g, 5 mmol) in methanol (8 mL) was added acetic acid (0.28 mL) and the solution was stirred at RT for 1 h. Sodium cyanoborohydride (310 mg, 5 mmol) was added and the reaction mixture was stirred at 45° C. overnight and then 1 N NaOH (5 mL) was added. The aqueous phase was extracted with EtOAc (3×15 mL). The combined organic extracts were washed with brine, dried over MgSO4, filtered, concentrated under vacuum, and purified by silica gel chromatography (0-5% MeOH/DCM). Pure fractions were combined and concentrated under vacuum to provide the title intermediate (0.71 g, 30% yield) as a clear oil. (m/z): [M+H]+ calcd for C23H35N3O4 418.26 found 418.1.

Workup

  1. stirringthe reaction mixture was stirred at 45° C. overnight
  2. extractionThe aqueous phase was extracted with EtOAc (3×15 mL)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. custompurified by silica gel chromatography (0-5% MeOH/DCM)
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-660354e46fbe40568b1b4e003a0132ac
Source dataset
uspto-grants-2015_12
Patent number
US09206159B2

Reaction notes

Loading…