2-Pyrrolidinemethanol, alpha,alpha-diphenyl-, (S)- → (1S,4S)-1,4-bis(4-nitrophenyl)butane-1,4-diol

HRID 2364791

Reaktionsgleichung

Reaktionsgleichung von HRID 2364791
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:24])[CH2:11][CH2:12][C:13]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)=[O:14])=[CH:6][CH:5]=1)([O-:3])=[O:2].C1(C(C2C=CC=CC=2)([C@@H]2CCCN2)O)C=CC=CC=1>>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]([OH:24])[CH2:11][CH2:12][C@@H:13]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)[OH:14])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Komponenten

3

Edukt 2

HCID 27248992-Pyrrolidinemethanol, alpha,alpha-diphenyl-, (S)-HCID 137628911,4-Bis(4-nitrophenyl)butane-1,4-dione

Produkt 1

HCID 59616963(1S,4S)-1,4-bis(4-nitrophenyl)butane-1,4-diolAusbeute 66,3 %

Versuchsvorschrift

The product from Example 1A (30 g, 95 wt %, 91.4 mmol) was subjected to the conditions described in Example 32, substituting (R)-(−)-α,α-diphenyl-2-pyrrolidinemethanol for (S)-(−)-α,α-diphenyl-2-pyrrolidinemethanol, to give the title compound (20.14 g, >99.55 ee, 61% yield) which was contaminated with 9.7% of the meso isomer (vs. dl isomer).

Quellen und Nachweise

ORD-Eintrag
ord-6063b9267a044a2fb3df49b0fce5ba8b
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08691938B2

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