Dichloromethane → 4-Amino-4-(3-ethoxy-4-methoxyphenyl)butan-2-ol hydrochloride

HRID 1661747Notes

Reaction equation

HRID 1661747 reaction equation
C(OC([NH:8][CH:9]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH2:23][CH3:24])[CH:15]=1)[CH2:10][CH:11]([OH:13])[CH3:12])=O)(C)(C)C.O1CCOCC1.C(Cl)[Cl:32]>>[ClH:32].[NH2:8][CH:9]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH2:23][CH3:24])[CH:15]=1)[CH2:10][CH:11]([OH:13])[CH3:12]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 312751,4-DioxaneHCID 131724264Tert-butyl (1-(3-ethoxy-4-methoxyphenyl)-3-hydroxybutyl)carbamate

Product 1

HCID 187583154-Amino-4-(3-ethoxy-4-methoxyphenyl)butan-2-ol hydrochlorideYield 85%

Procedure

A mixture of (tert-butoxy)-N-[1-(3-ethoxy-4-methoxyphenyl)-3-hydroxybutyl]carboxamide (0.98 g, 2.89 mmol) and 4Nhydrochloric acid/dioxane (3 mL) in methylene chloride (10 mL) was stirred at room temperature for 16 hours. The resulting slurry was filtered and washed with ethyl acetate to give 4-amino-4-(3-ethoxy-4-methoxyphenyl)butan-2-ol hydrochloride as a white solid (0.68 g, 85%); 1H NMR (D2O) δ 7.12 (m, 3H), 4.47 (t, J=7.0 Hz, 1H), 4.20 (q, J=7.4 Hz, 2H), 3.90 (s, 3H), 3.83-3.76 (m, 1H), 2.21-2.15 (m, 2H), 1.43 (t, J=6.9 Hz, 3H), 1.24 (d, J=6.1 Hz, 3H); 13C NMR (D2O) δ 151.75, 150.48, 131.92, 123.09, 115.05, 114.54, 67.86, 66.98, 58.53, 55.35, 44.41, 24.49, 16.68.

Workup

  1. filtrationThe resulting slurry was filtered
  2. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-dad7aec8dd414b4e99264448972d25de
Source dataset
uspto-grants-2011_10
Patent number
US08030343B2

Reaction notes

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