Acetic Acid → HCID 67246989, compound

HRID 2273181Notes

Reaction equation

HRID 2273181 reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:15][O:16][C:17]1[CH:18]=[C:19]2[C:28](=[CH:29][CH:30]=1)[N:27]=[CH:26][C:25]1[O:24][CH2:23][C:22](=O)[CH2:21][C:20]2=1.C(O)(=O)C.C([BH3-])#N.[Na+]>ClCCCl.O1CCCC1.CO>[C:1]([O:5][C:6](=[O:14])[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([CH:22]2[CH2:21][C:20]3[C:19]4[C:28](=[CH:29][CH:30]=[C:17]([O:16][CH3:15])[CH:18]=4)[N:27]=[CH:26][C:25]=3[O:24][CH2:23]2)[CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 7238334-(N-Boc-amino)piperidineHCID 5003444Sodium cyanoborohydrideHCID 67247636HCID 67247636, compound

Product 1

HCID 67246989HCID 67246989, compoundYield 6.4%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of piperidin-4-yl-carbamic acid tert-butyl ester (76 mg, 0.38 mmol, 1.0 eq) in 1,2-dichloroethane (1 mL) is added at room temperature to a stirred solution of 6-methoxy-4H-1-oxa-9-aza-phenanthrene-3-one (87 mg, 0.38 mmol, 1.0 eq) in tetrahydrofuran (6 mL), followed by acetic acid (5 μL, 0.08 mmol, 0.2 eq) and the resulting mixture is heated under reflux for 3 hours. The reaction mixture is then cooled down to room temperature before the addition of a solution of sodium cyanoborohydride (48 mg, 0.76 mmol, 2.0 eq) in methanol (1 mL). After 15 hours stirring at room temperature, solvents are evaporated and to give a residue that is purified by preparative HPLC to afford [1-(6-methoxy-3,4-dihydro-2H-1-oxa-9-aza-phenanthrene-3-yl)-piperidin-4-yl]-carbamic acid tert-butyl ester as a light yellow solid (10 mg, 6% yield).

Workup

  1. temperaturethe resulting mixture is heated
  2. temperatureunder reflux for 3 hours
  3. customsolvents are evaporated
  4. customto give a residue that
  5. customis purified by preparative HPLC

Sources & evidence

ORD record
ord-61ba2a730166461aa1e3585cb2b487dd
Source dataset
uspto-grants-2015_09
Patent number
US09120822B2

Reaction notes

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