Triethylborane → Methyl (E)-7-{2-(4-fluoro-3-methylphenyl)-4-(pyrrolidin-1-yl)-6,6-dimethylcyclohex-1-en-1-yl}-3,5-dihydroxyhept-6-enoate

HRID 654544Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 654544
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH:12]([N:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)[CH2:11][C:10]([CH3:20])([CH3:19])[CH:9]=2)=[CH:4][C:3]=1[CH3:21].[C:22](=[O:25])=[CH:23][CH3:24].[Li+].CC([N-]C(C)C)C.[C:34]([O:40][CH3:41])(=[O:39])[CH2:35][C:36]([CH3:38])=[O:37].C(B(CC)CC)C.[BH4-].[Na+]>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH:12]([N:14]3[CH2:15][CH2:16][CH2:17][CH2:18]3)[CH2:11][C:10]([CH3:19])([CH3:20])[C:9]=2/[CH:24]=[CH:23]/[CH:22]([OH:25])[CH2:38][CH:36]([OH:37])[CH2:35][C:34]([O:40][CH3:41])=[O:39])=[CH:4][C:3]=1[CH3:21]

Komponenten

7

Edukt 5

HCID 7357TriethylboraneHCID 7757Methyl acetoacetateHCID 2724682Lithium diisopropylamideHCID 4311764Sodium borohydrideHCID 867460012-(4-Fluoro-3-methylphenyl)-4-(pyrrolidin-1-yl)-6,6-dimethylcyclohex-1-en 1-propenal

Produkt 1

HCID 86744089Methyl (E)-7-{2-(4-fluoro-3-methylphenyl)-4-(pyrrolidin-1-yl)-6,6-dimethylcyclohex-1-en-1-yl}-3,5-dihydroxyhept-6-enoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

In a manner similar to Scheme I, 33 (2.27 g, 6,65 mmol) was treated with the LDA derived anion of methyl acetoacetate (7.98 mmol) followed by triethylborane, methanol, and NaBH4. Workup and purification by HPLC using 1% Et3N in EtOAc as eluent provided the oily product.

Aufarbeitung

  1. customWorkup and purification by HPLC
  2. customprovided the oily product

Quellen und Nachweise

ORD-Eintrag
ord-85874b406056472ca6300235678a06c6
Quelldatensatz
uspto-grants-1992_07
Patentnummer
US05132312

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