1,4-Dioxane → Tert-butyl 3-amino-3-cyclopropyl-butanoate

HRID 1480292Notes

Reaction equation

HRID 1480292 reaction equation
C(S([NH:7][C:8]([CH:18]1[CH2:20][CH2:19]1)([CH3:17])[CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=O)(C)(C)C.O1CCOCC1>Cl.C(OCC)(=O)C>[NH2:7][C:8]([CH:18]1[CH2:19][CH2:20]1)([CH3:17])[CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:14])[CH3:15])=[O:11]

Participants

5

Reactant 2

HCID 312751,4-DioxaneHCID 90203664Tert-butyl 3-(tert-butylsulfinylamino)-3-cyclopropyl-butanoate

Product 1

HCID 90203892Tert-butyl 3-amino-3-cyclopropyl-butanoateYield 85.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-butyl 3-(tert-butylsulfinylamino)-3-cyclopropyl-butanoate (example 229a, 1.93 g, 6.36 mmol) was dissolved in a 4M solution of hydrochloric acid in dioxane (4.77 ml, 19.1 mmol) and the reaction mixture was stirred at room temperature for 30 minutes. The reaction was then diluted with ethyl acetate and poured into a separatory funnel. The organic phase was extracted with a 2M aqueous solution of sodium carbonate. The organic phase was dried over sodium sulfate and evaporated down to dryness to yield the title compound (1.08 g, 85%) as a crude oil which was used without any purification. MS (ESI, m/z): 200.3 (M+H+).

Workup

  1. additionpoured into a separatory funnel
  2. extractionThe organic phase was extracted with a 2M aqueous solution of sodium carbonate
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. customevaporated down to dryness

Sources & evidence

ORD record
ord-f720ff10c27149b08bdea3c9ae4fd4e9
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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