Reaktion #660895

ord-641f0fb2e99e4e129ae110a5013a913a

Reaktionsgleichung

CC(C)c1nc2c(c(I)c1C=O)[C@@H](O[Si](C)(C)C(C)(C)C)CC(C)(C)C2
(S)-5-(tert-butyldimethylsilyloxy)-4-iodo-2-isopropyl-7,7-dimethyl-5,6,7,8-tetrahydroquinoline-3-carbaldehyde
O=C([O-])[O-].[Cs+].[Cs+]
caesium carbonate
[Cs+].[F-]
caesium fluoride
C[CH](C)[Mg][Cl]
isopropylmagnesium chloride
CC(C)Oc1ccc(I)cc1
1-iodo-4-isopropoxybenzene
C[CH](C)[Mg][Cl].[Cl-].[Li+]
isopropylmagnesium chloride lithium chloride
→
CC(C)Oc1ccc([C@H](O)c2c(C(C)C)nc3c(c2I)[C@@H](O[Si](C)(C)C(C)(C)C)CC(C)(C)C3)cc1
(S)—((S)-5-(tert-butyldimethylsilyloxy)-4-iodo-2-isopropyl-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-3-yl)(4-isopropoxyphenyl)methanol

Edukte

CC(C)c1nc2c(c(I)c1C=O)[C@@H](O[Si](C)(C)C(C)(C)C)CC(C)(C)C2
(S)-5-(tert-butyldimethylsilyloxy)-4-iodo-2-isopropyl-7,7-dimethyl-5,6,7,8-tetrahydroquinoline-3-carbaldehyde
—
solution
O=C([O-])[O-].[Cs+].[Cs+]
caesium carbonate
—
solution
[Cs+].[F-]
caesium fluoride
C[CH](C)[Mg][Cl]
isopropylmagnesium chloride
CC(C)Oc1ccc(I)cc1
1-iodo-4-isopropoxybenzene
—
solution
C[CH](C)[Mg][Cl].[Cl-].[Li+]
isopropylmagnesium chloride lithium chloride

Reagenzien

Keine

Lösungsmittel

C1CCOC1
tetrahydrofurane
O
water
C1CCOC1
tetrahydrofurane

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeObtained

Vorschrift

Obtained by starting from (S)-5-(tert-butyldimethylsilyloxy)-4-iodo-2-isopropyl-7,7-dimethyl-5,6,7,8-tetrahydroquinoline-3-carbaldehyde and 1-iodo-4-isopropoxybenzene. A 2 M solution of caesium carbonate in water is used instead caesium fluoride. A 1.3 M solution of isopropylmagnesium chloride-lithium chloride-complex in tetrahydrofurane is used instead of a 2 M solution of isopropylmagnesium chloride in tetrahydrofurane.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09029544B2uspto-grants-2015_05