Sodium borohydride → Methyl 7-[2-(2-hydroxy-2-methylheptylthio)-5-oxopyrrolidin-1-yl]-6-hydroxyheptanoate

HRID 371336Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 371336
[OH:1][C:2]([CH3:27])([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:3][S:4][CH:5]1[CH2:9][CH2:8][C:7](=[O:10])[N:6]1[CH2:11][C:12](=[O:21])[CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18].[BH4-].[Na+]>C(O)C>[OH:1][C:2]([CH3:27])([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:3][S:4][CH:5]1[CH2:9][CH2:8][C:7](=[O:10])[N:6]1[CH2:11][CH:12]([OH:21])[CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18]

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 20273770Methyl 7-[2-(2-hydroxy-2-methylheptylthio)-5-oxopyrrolidin-1-yl]-6-oxoheptanoate

Produkt 1

HCID 20273773Methyl 7-[2-(2-hydroxy-2-methylheptylthio)-5-oxopyrrolidin-1-yl]-6-hydroxyheptanoateAusbeute 67,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 16 (about 4 mg) in ethanol (0.5 mL) at 0° was added sodium borohydride (3 mg). The mixture was stirred at 0° for one hour and then quenched with one drop of acetic acid. After removing ethanol, the residue was diluted with methylene chloride and washed with saturated sodium chloride. The separated aqueous layer was extracted with methylene chloride twice and the combined organic layer was dried over magnesium sulfate. Removal of the solvent gave 2.7 mg of methyl 7-[2-(2-hydroxy-2-methylheptylthio)-5-oxopyrrolidin-1-yl]-6-hydroxyheptanoate, 17. By comparison of TLC mobility, this product was determined to be identical in element content to that of Example 4.

Aufarbeitung

  1. customquenched with one drop of acetic acid
  2. customAfter removing ethanol
  3. additionthe residue was diluted with methylene chloride
  4. washwashed with saturated sodium chloride
  5. extractionThe separated aqueous layer was extracted with methylene chloride twice
  6. dry with materialthe combined organic layer was dried over magnesium sulfate
  7. customRemoval of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-d7dfa36269804f8f96af0a140e4ae333
Quelldatensatz
uspto-grants-1985_07
Patentnummer
US04530933

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