Ammonium Chloride → (S)-7-bromo-2-(1-tert-butoxy-2-hydroxyethyl)-3-methylnaphthalen-1-ol

HRID 926163Notes

Reaction equation

[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH3:32])[C:8]([C@H:13]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[C:14](O[C@@H]3C[C@H](C)CC[C@H]3C(C)C)=[O:15])=[C:9]2[OH:12])=[CH:4][CH:3]=1.C([BH-](CC)CC)C.[Li+].[NH4+].[Cl-]>C1COCC1>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH3:32])[C:8]([C@H:13]([O:27][C:28]([CH3:30])([CH3:29])[CH3:31])[CH2:14][OH:15])=[C:9]2[OH:12])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 55 °C

Procedure

To a solution of (S)-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl) 2-(7-bromo-1-hydroxy-3-methylnaphthalen-2-yl)-2-tert-butoxyacetate (4.56 g, 9.02 mmol) in THF (45 mL) was added lithium triethylborohydride solution (Super Hydride, 1.0 M in THF, 36 mL, 36 mmol). The reaction was stirred at 55° C. for 2.5 h. A saturated solution of NH4Cl was added. The layers were separated, and the organic layer was dried, filtered, and concentrated in vacuo. The crude material was purified by column chromatography (EtOAc/hexanes) to give 2.84 g. 1H-NMR: 400 MHz, (CDCl3) δ: 9.77 (s, 1H), 8.37 (s, 1H), 7.50 (m, 2H), 7.10 (s, 1H), 5.26 (dd, J=9, 4 Hz, 1H), 4.20 (m, 2H), 2.48 (s, 3H), 1.25 (s, 9H) 1.21 (s, 9H).

Workup

customThe layers were separated
customthe organic layer was dried
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude material was purified by column chromatography (EtOAc/hexanes)
customto give 2.84 g

Sources & evidence

ORD record: ord-bd4dbc531f2e4e13aa6897aee82b82a1
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09284323B2

Reaction notes

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