Hydrochloric Acid → HCID 22673290, compound

HRID 1385580Notes

Reaction equation

[C:1]([N:6]1[C:11](=[O:12])[CH:10]2[CH2:13][CH:7]1[CH:8]=[CH:9]2)(=[O:5])[CH:2]([CH3:4])[CH3:3].[BH4-].[Na+].Cl.[OH-].[Na+]>O.CC(O)CC>[C:1]([NH:6][CH:7]1[CH2:13][CH:10]([CH2:11][OH:12])[CH:9]=[CH:8]1)(=[O:5])[CH:2]([CH3:4])[CH3:3]

Participants

Conditions

Temperature: 20 °C

Procedure

9 g of (±)-2-isobutyryl-2-azabicyclo[2.2.1]hept-5-en-3-one were dissolved in water (32 ml) and 2-butanol (84 ml) under nitrogen and cooled to 0° C. 1.37 g of sodium borohydride were added in portions over the course of 3.5 h. The mixture was stirred for a further 3 h at 20° C., and it was then adjusted to pH 2.5 with a mixture of conc. hydrochloric acid and water (1/1) and then neutralized with 2N NaOH. The solution was evaporated to 40 g. The residue was extracted with 3×80 ml of dichloromethane. The combined organic phases were completely evaporated. The resulting solid was crystallized in 25 ml of toluene. 6.8 g of title compound were obtained. The yield was 73.6%.

Workup

customThe solution was evaporated to 40 g
extractionThe residue was extracted with 3×80 ml of dichloromethane
customThe combined organic phases were completely evaporated
customThe resulting solid was crystallized in 25 ml of toluene

Sources & evidence

ORD record: ord-5fc38d8d8c0a4aba942316ee014fdf52
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06262295B1

Reaction notes

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