Dimethyl Sulfide → Tert-butyl 4,4-difluoro-2-(hydroxymethyl)pyrrolidine-1-carboxylate

HRID 350497

Reaktionsgleichung

Reaktionsgleichung von HRID 350497
[C:1]([O:5][C:6]([N:8]1[CH2:15][C:14]([F:17])([F:16])[CH2:13][C@H:9]1[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].CSC>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:15][C:14]([F:16])([F:17])[CH2:13][CH:9]1[CH2:10][OH:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 1068Dimethyl SulfideHCID 22977458(2S)-1-[(tert-butoxy)carbonyl]-4,4-difluoropyrrolidine-2-carboxylic acid

Produkt 1

HCID 22001352Tert-butyl 4,4-difluoro-2-(hydroxymethyl)pyrrolidine-1-carboxylateAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of N-(tert-butoxycarbonyl) 4,4-difluoroproline (3.00 g, 11.9 mmol) in THF (20 ml) was added BH3.DMS (1. 1 ml, 11.9 mmol) at room temperature. The mixture was heated at reflux for 2 h. After cooling to room temperature, the mixture was concntrated in vacuo. The residue was quenched by the addition of H2O (100 ml) and extracted with CHCl3 (2×200 ml). The combined extracts were dried over MgSO4 and evaporated. The residue was chromatographed on silica gel with CHCl3-EtOAc (4:1) as eluent to give 1-(tert-butoxycarbonyl)-4,4-difluoro-2-pyrrolidinylmethanol (2.11 g, 75%) as a colorless oil. 1H-NMR (CDCl3) δ 1.48 (s, 9 H), 2.04–2.55 (m, 2 H), 3.59–4.17 (m, 5 H).

Aufarbeitung

  1. customat room temperature
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 2 h
  4. customThe residue was quenched by the addition of H2O (100 ml)
  5. extractionextracted with CHCl3 (2×200 ml)
  6. dry with materialThe combined extracts were dried over MgSO4
  7. customevaporated
  8. customThe residue was chromatographed on silica gel with CHCl3-EtOAc (4:1) as eluent

Quellen und Nachweise

ORD-Eintrag
ord-bb5d5825beea47409329f47aa7eae666
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07179819B2

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