Potassium Hydroxide → (SR)-2-((RS)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-(methylthio)propan-1-amine

HRID 390090Notes

Reaction equation

HRID 390090 reaction equation
[CH3:1][C:2]1([CH3:23])[O:6][CH:5]([CH:7]([CH2:20][S:21][CH3:22])[CH2:8][NH:9]C(=O)OCC2C=CC=CC=2)[CH2:4][O:3]1.[OH-].[K+]>C(O)(C)C.C(Cl)Cl>[NH3:9].[CH3:2][OH:3].[CH3:1][C:2]1([CH3:23])[O:6][CH:5]([CH:7]([CH2:20][S:21][CH3:22])[CH2:8][NH2:9])[CH2:4][O:3]1

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 86651336HCID 86651336, compound

Product 2

HCID 21705897Ammonia methanolYield 7%HCID 66953476(SR)-2-((RS)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-(methylthio)propan-1-amineYield 166%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of benzyl (SR)-2-((RS)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-(methylthio)propylcarbamate (50 mg, 147 μmol) and potassium hydroxide (248 mg, 4419 μmol) in isopropanol (2 mL) was heated under reflux for 2 h. Silica gel was added and the mixture was concentrated to dryness, then applied to a silica gel column and eluted with 5% MeOH/CH2Cl2, then 7% 7N NH3/MeOH in CH2Cl2 to give (SR)-2-((RS)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-(methylthio)propan-1-amine (25 mg, 122 μmol, 83% yield) as a syrup. 1H NMR (CDCl3) δ 4.20 (1H, dd, J=6.6, 13.5 Hz), 4.06 (1H, dd, J=6.3, 8.0 Hz); 3.70 (1H, t, J=7.7 Hz); 2.82-2.74 (3H, m); 2.61 (1H, dd, J=8.0, 13.0 Hz); 2.13 (3H, s); 1.85-1.75 (1H, m); 1.41 (3H, s); 1.35 (3H, s). 13C NMR (CDCl3) δ 109.1, 76.9, 67.9, 44.5, 42.3, 33.7, 26.9, 25.7, 16.8.

Workup

  1. temperatureunder reflux for 2 h
  2. additionSilica gel was added
  3. concentrationthe mixture was concentrated to dryness
  4. washeluted with 5% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-fed532626822435ab672a651a0cf3b84
Source dataset
uspto-grants-2013_02
Patent number
US08383636B2

Reaction notes

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