Sodium Hydroxide → (6-bromo-1-hydroxy-2,3-dihydro-1H-inden-2-yl)acetic Acid

HRID 2390396Notes

Reaction equation

[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH:7]([CH2:12][C:13]([O:15]CC)=[O:14])[C:8]2=[O:11])=[CH:4][CH:3]=1.C(NB)(C)(C)C.[OH-].[Na+]>C1COCC1>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH:7]([CH2:12][C:13]([OH:15])=[O:14])[CH:8]2[OH:11])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 42.5 °C

Procedure

The product from Example 52A in THF was treated with tert-butylaminoborane (1.18 g, 13.5 mmol) and heated at 40-45° C. for 2.5 hours. The mixture was treated with sodium hydroxide solution (1.8 g in water, 40 mL) and heating was continued for 30 minutes. The mixture was allowed to cool to room temperature and the aqueous layer was separated. The organic layer was diluted with isopropyl acetate (40 mL) and water (40 mL) and combined with the aqueous layer. The solution was cooled to 0° C. and the pH was adjusted to 2 by addition of concentrated hydrochloric acid. The mixture was filtered and the filter cake dried at room temperature. The solid was slurried in dichloromethane (6 mL), refiltered, and redried to provide the title compound.

Workup

temperatureheating
temperatureto cool to room temperature
customthe aqueous layer was separated
additionThe organic layer was diluted with isopropyl acetate (40 mL) and water (40 mL)
temperatureThe solution was cooled to 0° C.
additionthe pH was adjusted to 2 by addition of concentrated hydrochloric acid
filtrationThe mixture was filtered
customthe filter cake dried at room temperature
customredried

Sources & evidence

ORD record: ord-7c153e8efb714476ae393eb257b61401
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273767B2

Reaction notes

Loading…