tert-Butoxy bis(dimethylamino)methane → HCID 86725587, compound

HRID 514466Notes

Reaction equation

HRID 514466 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:16][N:17]([CH3:27])[CH:18](OC(C)(C)C)N(C)C>CN(C=O)C>[Si:1]([O:8][CH2:9][CH2:10]/[C:11](=[CH:16]\[N:17]([CH3:27])[CH3:18])/[C:12]([O:14][CH3:15])=[O:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 15399104Methyl 4-{[tert-butyl(dimethyl)silyl]oxy}butanoate

Product 1

HCID 86725587HCID 86725587, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of methyl 4-[tert-butyl(dimethyl)silyl]oxybutanoate (6.8 g, 29.31 mmol) and N,N,N′,N′-tetramethyl-1-[(2-methylpropan-2-yl)oxy]methanediamine (5.1 g, 29.31 mmol) in DMF (14 mL) in sealed tube was heated to 100° C. overnight. Added water to the mixture at 0° C. and extracted with ethyl acetate twice. The organic phase was separated and washed with water (2×) and brine and dried with anhydrous Na2SO4. The organic phase was concentrated to give the title compound (7.33 g, 91%). [M+H] Calc'd for C14H29NO3Si, 288. Found, 288.

Workup

  1. extractionAdded water to the mixture at 0° C. and extracted with ethyl acetate twice
  2. customThe organic phase was separated
  3. washwashed with water (2×) and brine
  4. dry with materialdried with anhydrous Na2SO4
  5. concentrationThe organic phase was concentrated

Sources & evidence

ORD record
ord-b250a9af975645f78eeb05211c9031d2
Source dataset
uspto-grants-2015_08
Patent number
US09107916B2

Reaction notes

Loading…