Sodium borohydride → N-(tert-butyl)-1-(hydroxymethyl)cyclopropane-1-sulfonamide

HRID 1852056Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1852056
[C:1]([NH:5][S:6]([C:9]1([CH:12]=[O:13])[CH2:11][CH2:10]1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO.[Cl-].[Na+].O>[C:1]([NH:5][S:6]([C:9]1([CH2:12][OH:13])[CH2:10][CH2:11]1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 2

HCID 4311764Sodium borohydrideHCID 86683169N-(1,1-Dimethylethyl)-1-formylcyclopropanesulfonamide

Produkt 1

HCID 71004881N-(tert-butyl)-1-(hydroxymethyl)cyclopropane-1-sulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A round-bottom flask equipped with a stir bar was charged with a solution of N-(tert-butyl)-1-formylcyclopropane-1-sulfonamide (8.89 g, 43.3 mmol) in MeOH (110 mL). The solution was cooled to 0° C. and to the solution was added portionwise sodium borohydride (1.64 g, 43.3 mmol). The solution was stirred for 1 h. To the solution was added brine and the mixture was stirred for 15 min. The mixture was concentrated in vacuo to remove MeOH and the aqueous solution was then transferred to separatory funnel and was twice extracted with EtOAc. The combined organics were washed with sat. aq. NaCl; dried over MgSO4; filtered; and then concentrated in vacuo to afford N-(tert-butyl)-1-(hydroxymethyl)cyclopropane-1-sulfonamide as a colorless, crystalline solid (8.66 g, 96%). 1H NMR (400 MHz, CDCl3) δ 4.35 (br. s., 1H), 3.86 (d, J=6.0 Hz, 2H), 2.77 (t, J=6.0 Hz, 1H), 1.50-1.45 (m, 2H), 1.39 (s, 9H), 1.06-1.01 (m, 2H).

Aufarbeitung

  1. customA round-bottom flask equipped with a stir bar
  2. stirringthe mixture was stirred for 15 min
  3. concentrationThe mixture was concentrated in vacuo
  4. customto remove MeOH
  5. customthe aqueous solution was then transferred to separatory funnel
  6. extractionwas twice extracted with EtOAc
  7. washThe combined organics were washed with sat. aq. NaCl
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationand then concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c55b5ee365264734b22bb5cbe2b50c17
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957203B2

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