Dimethyl Sulfate → N-Boc-1-methoxy-2-methyl-2-propanamine

HRID 82279Notes

Reaction equation

HRID 82279 reaction equation
[OH-].[K+].[C:3]([O:7][C:8](=[O:15])[NH:9][C:10]([CH3:14])([CH3:13])[CH2:11][OH:12])([CH3:6])([CH3:5])[CH3:4].S(OC)(O[CH3:20])(=O)=O>O1CCOCC1>[C:3]([O:7][C:8](=[O:15])[NH:9][C:10]([CH3:14])([CH3:13])[CH2:11][O:12][CH3:20])([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 14797Potassium HydroxideHCID 14578673tert-butyl N-(1-hydroxy-2-methylpropan-2-yl)carbamate

Product 1

HCID 21255687N-Boc-1-methoxy-2-methyl-2-propanamineYield 88%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

KOH (3.47 g, 61.82 mmol) was added to a solution of (2-Hydroxy-1,1-dimethyl-ethyl)-carbamic acid tert-butyl ester (Preparation 253, 3.9 g, 20.6 mmol) in 1,4-dioxane (30 mL) followed by the slow addition of dimethyl sulphate at room temperature. The mixture was further allowed to stir at room temperature for 48 hours. Reaction mass was filtered through a short pad of celite, washed with DCM (3×50 mL). The combined filtrate was washed with water (2×50 mL), brine (30 mL), dried over sodium sulphate and evaporated in vacuo to afford the title compound as yellow oil in 88% yield, 3.7 g.

Workup

  1. customReaction mass
  2. filtrationwas filtered through a short pad of celite
  3. washwashed with DCM (3×50 mL)
  4. washThe combined filtrate was washed with water (2×50 mL), brine (30 mL)
  5. dry with materialdried over sodium sulphate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-72f2dbe78faf4edbb6c33f91bdd6f0a2
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

Loading…