Lithium Hydroxide → (R)-2-[6-(4-tert-butyl-cyclohexyloxy)-naphthalen-2-yl]-2-methylamino-propan-1-ol

HRID 1036437Notes

Reaction equation

[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[C:17]([C@:22]2([CH3:29])[CH2:26][O:25][C:24](=O)[N:23]2C)[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-]>C(O)C>[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[C:17]([C@:22]([NH:23][CH3:24])([CH3:29])[CH2:26][OH:25])[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of (R)-4-[6-(4-tert-butyl-cyclohexyloxy)-naphthalen-2-yl]-3,4-dimethyl-oxazolidin-2-one (80 mg, 0.2 mmol) in 4.2 M of LiOH aqueous (1.5 mL, 6 mmol) and ethanol (1.5 mL) was heated at 120° C. for 5 hrs. The solvent was concentrated and the residue was washed with water to give white precipitate. The crude was purified with silica gel column eluted with 2 M NH3 in MeOH and DCM from 0 to 8% to give 7 mg of product, 10%. ESI-MS (M−30)+: 339.30, room temperature 1.57 min. 1H NMR (400 MHz, CDCl3) δ: 7.76˜7.70 (m, 3H), 7.51 (d, 1H), 7.17-7.12 (m, 2H), 4.27 (m, 1H), 3.88 (d, 1H), 3.71 (d, 1H), 2.32-2.23 (m, 5H), 1.89 (d, 2H), 1.62 (s, 3H), 1.44 (m, 2H), 1.25˜1.05 (m, 3H), 0.90 (s, 9H)

Workup

concentrationThe solvent was concentrated
washthe residue was washed with water
customto give white precipitate
customThe crude was purified with silica gel column
washeluted with 2 M NH3 in MeOH and DCM from 0 to 8%

Sources & evidence

ORD record: ord-d224c0f599a64203806500953cdbe48e
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546359B2

Reaction notes

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