Water → HCID 69067548, compound

HRID 553967Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C@H:10]2[N:19]3[C@H:14]([CH2:15][CH2:16][CH2:17][C:18]3=[O:20])[CH2:13][C@@H:12]3[O:21][C@H:11]23)[CH:5]=[C:6]([F:9])[C:7]=1[F:8].C([BH-](CC)CC)C.[Li+].O.C(OCC)(=O)C>C1COCC1>[OH:21][C@H:11]1[CH2:12][CH2:13][C@@H:14]2[N:19]([C:18](=[O:20])[CH2:17][CH2:16][CH2:15]2)[C@@H:10]1[C:4]1[CH:3]=[C:2]([F:1])[C:7]([F:8])=[C:6]([F:9])[CH:5]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of (1aR*,2R*,6aR*,7aS*)-2-(3,4,5-trifluorophenyl)octahydro-1-oxa-2a-aza-cyclopropa[b]naphthalen-3-one (123 mg) in THF (4.0 mL) was cooled to −78° C. Lithium triethyl borohydride (1 M solution in THF, 620 μL) was added to the reaction solution, which was then stirred at 0° C. for one hour. Water and ethyl acetate were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system->ethyl acetate-methanol system) to obtain 125 mg of the title compound. The property values of the compound are as follows.

Workup

customthe organic layer was separated
washThe resulting organic layer was washed with brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system->ethyl acetate-methanol system)

Sources & evidence

ORD record: ord-d3f962fe17c747a5a922a5688b2cc8f3
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08048878B2

Reaction notes

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