Acetic Acid → HCID 11379291, compound

HRID 2364107Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.[O:12]1[C:16]2([CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]2)[O:15][CH2:14][CH2:13]1.[BH3-]C#N.[Na+].[OH-].[Na+]>CO>[C:2]1([NH:1][CH:19]2[CH2:20][CH2:21][C:16]3([O:15][CH2:14][CH2:13][O:12]3)[CH2:17][CH2:18]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of aniline (0.58 mL, 6.4 mmol) and acetic acid (0.73 mL, 12.8 mmol) in MeOH (6 mL) was added 1,4-dioxaspiro[4.5]decan-8-one (1.0 g, 6.4 mmol). The mixture was stirred at 50° C. for 2 h. Then, NaCNBH3 (402 mg, 6.4 mmol) was added at 0° C. The mixture was stirred at room temperature for 2 h. Then, 2 M aqueous NaOH was added to quench the reaction. The organic materials were extracted with EtOAc. The combined extracts were washed with brine, dried over Na2SO4 and filtered. After removal of the solvent at reduced pressure, the residue was purified by column chromatography (Purif, silica gel, 95:5 hexane/EtOAc to 70:30 hexane/EtOAc) to give the crude title compound (1.39 g, 93%) as a pale yellow solid:

Workup

stirringThe mixture was stirred at room temperature for 2 h
customto quench
customthe reaction
extractionThe organic materials were extracted with EtOAc
washThe combined extracts were washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
customAfter removal of the solvent at reduced pressure
customthe residue was purified by column chromatography (Purif, silica gel, 95:5 hexane/EtOAc to 70:30 hexane/EtOAc)

Sources & evidence

ORD record: ord-a9dad68f9d7e4b45bed04c6e10be85ce
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691828B2

Reaction notes

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