Acetic Acid → HCID 117701770, compound

HRID 1507432Notes

Reaction equation

HRID 1507432 reaction equation
Cl.[OH:2][C:3]1[C:12]([CH3:13])=[C:11]2[C:6]([C:7](=[O:20])[C:8]([CH3:19])=[C:9]([C@H:14]3[CH2:18][CH2:17][CH2:16][NH:15]3)[O:10]2)=[CH:5][CH:4]=1.C=O.S([O-])([O-])(=O)=O.[Mg+2].[C:29](O)(=O)C.C([BH3-])#N.[Na+]>>[OH:2][C:3]1[C:12]([CH3:13])=[C:11]2[C:6]([C:7](=[O:20])[C:8]([CH3:19])=[C:9]([C@H:14]3[CH2:18][CH2:17][CH2:16][N:15]3[CH3:29])[O:10]2)=[CH:5][CH:4]=1

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 712FormaldehydeHCID 24083Sulfuric acid magnesium salt (1:1)HCID 5003444Sodium cyanoborohydrideHCID 117701579HCID 117701579, compound

Product 1

HCID 117701770HCID 117701770, compoundYield 28%

Conditions

Temperature
50 °C

Procedure

A mixture composed of 7-hydroxy-3,8-dimethyl-2-[(2R)-pyrrolidin-2-yl]-4H-chromen-4-one hydrochloride (78 mg, 0.30 mmol) obtained in Example 2-3, 90% paraformaldehyde (50 mg, 1.50 mmol), magnesium sulfate (60 mg), and acetic acid (17 μL, 0.30 mmol) was stirred at 50° C. for 5 minutes. Then, sodium cyanoborohydride (43 mg, 0.66 mmol) was added thereto, and the mixture was stirred at 50° C. for 3 hours. Insoluble matter in the reaction solution was filtered off and then washed with methanol. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by reverse-phase HPLC to obtain 23 mg of the title compound (yield: 27%).

Workup

  1. stirringthe mixture was stirred at 50° C. for 3 hours
  2. filtrationInsoluble matter in the reaction solution was filtered off
  3. washwashed with methanol
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe obtained residue was purified by reverse-phase HPLC

Sources & evidence

ORD record
ord-dbca6d2996b948a6bf405aba140f6233
Source dataset
uspto-grants-2015_12
Patent number
US09221811B2

Reaction notes

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