Water → 5-Dimethylaminomethyl-6-(2-fluoro-5-hydroxy-phenyl)-spiro[2.5]octan-6-ol hydrochloride

HRID 2404609Notes

Reaction equation

O.C[Si]([Cl:6])(C)C.[CH3:7][N:8]([CH2:10][CH:11]1[C:18]([C:20]2[CH:25]=[C:24]([OH:26])[CH:23]=[CH:22][C:21]=2[F:27])([OH:19])[CH2:17][CH2:16][C:13]2([CH2:15][CH2:14]2)[CH2:12]1)[CH3:9]>CC(=O)CC>[ClH:6].[CH3:9][N:8]([CH2:10][CH:11]1[C:18]([C:20]2[CH:25]=[C:24]([OH:26])[CH:23]=[CH:22][C:21]=2[F:27])([OH:19])[CH2:17][CH2:16][C:13]2([CH2:15][CH2:14]2)[CH2:12]1)[CH3:7]

Participants

Conditions

Temperature: 0 °C

Procedure

Add H2O (9 mg, 0.500 mmol) and TMSCl (18 mg, 0.167 mmol) to a solution of 5-dimethylaminomethyl-6-(2-fluoro-5-hydroxy-phenyl)-spiro[2.5]octan-6-ol (41 mg, 0.139 mmol) in 2-butanone (30 mL). Stir the mixture at 0° C. for 2 hours. Concentrate the mixture under vacuum to give 5-dimethylaminomethyl-6-(2-fluoro-5-hydroxy-phenyl)-spiro[2.5]octan-6-ol hydrochloride as white solid (46 mg, Yield: 100%). 1H NMR (400 MHz, D2O) δ 7.13-7.15 (d, J1=6.8, J2=3.2, 1H), 6.93-6.98 (d, J1=12.0, J2=8.8, 1H), 6.69-6.73 (m, 1H), 3.05-3.10 (m, 1H), 2.65-2.76 (m, 8H), 2.44-2.45 (m, 1H), 2.27-2.35 (m, 2H), 1.70-1.74 (m, 1H), 0.96-0.98 (m, 1H), 0.79-0.82 (m, 1H), 0.45 (m, 1H).

Workup

concentrationConcentrate the mixture under vacuum

Sources & evidence

ORD record: ord-dbc39f926e744339acb73f6f736f15f0
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802728B2

Reaction notes

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