Sodium Hydroxide → HCID 54766095, compound

HRID 1503288Notes

Reaction equation

[CH3:1][N:2]([CH3:34])[CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH2:14][C@H:15]3[CH2:19][O:18]C(=O)[NH:16]3)[CH:12]=2)[N:7]([C:21]2[CH:26]=[CH:25][C:24]([O:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:23][CH:22]=2)[CH:6]=1.[OH-].[Na+]>C(O)C>[NH2:16][C@@H:15]([CH2:14][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[CH:23][CH:22]=1)[CH:6]=[C:5]2[CH2:4][CH2:3][N:2]([CH3:34])[CH3:1])[CH2:19][OH:18]

Participants

Conditions

Temperature: 80 °C

Procedure

(S)-2-Amino-3-[3-(2-(dimethylamino)ethyl)-1-(4-phenoxyphenyl)-1H-indol-5-yl]propan-1-ol (48) was prepared as follows: A mixture of compound 45 prepared in Example 11 (0.2 g, 0.4 mmol), 4 mL NaOH (2N aqueous) and 4 mL of ethanol was shaken at 80° C. for 2 hours. After cooling to room temperature, the reaction mixture was extracted with CHCl3, concentrated and purified by column (silica gel, EtOAc/MeOH/NH4OH 80/20/2) to give compound 48 as a sticky oil, which was dissolved in 10 mL of HCl (0.2N aqueous), and freeze dried to afford a white solid (110 mg, HCl-salt, ˜50%): 1H-NMR (400 MHz, CD3OD) δ: 7.72 (s, 1H), 7.49-7.54 (m, 4H), 7.4-7.44 (m, 2H), 7.16-7.22 (m, 4H), 7.07-7.11 (m, 2), 3.73-3.75 (m, 1H), 3.53-3.62 (m, 4H), 3.08-3.12 (m, 2H), 3.1 (s, 6H); LC/MS: m/z=430.1 [M+H]+ (Calc: 429.5).

Workup

custom(S)-2-Amino-3-[3-(2-(dimethylamino)ethyl)-1-(4-phenoxyphenyl)-1H-indol-5-yl]propan-1-ol (48) was prepared
temperatureAfter cooling to room temperature
extractionthe reaction mixture was extracted with CHCl3
concentrationconcentrated
custompurified by column (silica gel, EtOAc/MeOH/NH4OH 80/20/2)

Sources & evidence

ORD record: ord-5199daf8290d4cbbb0f2ed6eada48a6a
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212139B2

Reaction notes

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