Hydrochloric Acid → Benzyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate

HRID 41017Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 41017
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH:13]([C:16](O)=[O:17])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B.Cl>C1COCC1>[OH:17][CH2:16][CH:13]1[CH2:14][CH2:15][N:11]([C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[CH2:12]1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 185384831-N-Cbz-pyrrolidine-3-carboxylic acid

Produkt 1

HCID 18332648Benzyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 1-[(benzyloxy)carbonyl]pyrrolidine-3-carboxylic acid (1.0 g, 4.0 mmol) in THF (37 mL) at 0° C. was added dropwise a solution of 1.0 M borane in THF (16.4 mL). The reaction was allowed to warm to room temperature and stir for 16 hours. The mixture was cooled to 0° C. and 10% HCl (50 mL) was added. After the addition, the mixture was extracted with DCM, and the extract was washed sequentially with saturated NaHCO3 solution and brine, then dried over sodium sulfate, filtered and the solvent was removed in vacuo. The product was used without further purification in the subsequent oxidation step.

Aufarbeitung

  1. temperatureThe mixture was cooled to 0° C.
  2. additionAfter the addition
  3. extractionthe mixture was extracted with DCM
  4. washthe extract was washed sequentially with saturated NaHCO3 solution and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvent was removed in vacuo
  8. customThe product was used without further purification in the subsequent oxidation step

Quellen und Nachweise

ORD-Eintrag
ord-00eabaf7d3d14f6bb5c1947a3f6def4c
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530485B2

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