Diethyl Ether → HCID 89686408, compound

HRID 520427Notes

Reaction equation

HRID 520427 reaction equation
[CH3:1][C:2]([CH3:5])([O-:4])[CH3:3].[K+].Br[C:8](C)(C)[C:9]([NH:11][C:12]([CH3:15])([CH3:14])[CH3:13])=O.C[CH2:19][O:20]CC.[CH2:23]1COCC1>>[C:12]([NH:11][C:9]([CH3:8])([CH3:23])[C:19]([O:4][C:2]([CH3:5])([CH3:3])[CH3:1])=[O:20])([CH3:13])([CH3:14])[CH3:15]

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 8028TetrahydrofuranHCID 10878723Propanamide, 2-bromo-N-(1,1-dimethylethyl)-2-methyl-HCID 23665647Potassium tert-butoxide2×

Product 1

HCID 89686408HCID 89686408, compound

Procedure

A 1M solution of potassium tert-butoxide (3.00 mL, 3.00 mmol) in THF was added to a cold (0° C.) stirred solution of 2-bromo-N-(tert-butyl)-2-methylpropanamide (0.666 g, 3 mmol) in an. ether (30 mL) and the mixture was stirred at 0° C. for 2-3 h. Then 2nd equivalent of potassium tert-butoxide (3.00 mL, 3.00 mmol) was added and the mixture allowed to warm to rt and stirred overnight. The reaction was quenched with satd. NH4Cl, the organic layer was separated and washed with water, brine and dried (Na2SO4). The crude isolate was purified by silica gel FCC (3% MeOH in DCM) to afford tert-butyl 2-(tert-butylamino)-2-methylpropanoate (365 mg) as a light brown oil. 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 1.93 (br. s, 7H), 1.46 (s, 9H), 1.14 (s, 9H).

Workup

  1. customThe reaction was quenched with satd
  2. customNH4Cl, the organic layer was separated
  3. washwashed with water, brine
  4. dry with materialdried (Na2SO4)
  5. customThe crude isolate
  6. customwas purified by silica gel FCC (3% MeOH in DCM)

Sources & evidence

ORD record
ord-f39283f0c124424b96eca0e631e85c25
Source dataset
uspto-grants-2016_05
Patent number
US09326973B2

Reaction notes

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