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1,8-Diazabicyclo(5.4.0)undec-7-ene → (+/-)-(3aR*,8aS*)-1,2,3,3a,8,8a-Hexahydro-1,3a,8-trimethylpyrrolo-[2,3-b]indol-4-yl (R)-(alpha-methylbenzyl)carbamate

HRID 1770
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1770
[CH3:1][N:2]1[C@@H:6]2[N:7]([CH3:15])[C:8]3[CH:9]=[CH:10][CH:11]=[C:12]([OH:14])[C:13]=3[C@:5]2([CH3:16])[CH2:4][CH2:3]1.C1CCN2C(=NCCC2)CC1.[CH3:28][CH:29]([N:36]=[C:37]=[O:38])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C1COCC1>[CH3:28][C@@H:29]([NH:36][C:37](=[O:38])[O:14][C:12]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:13]=1[C@@:5]1([CH3:16])[CH2:4][CH2:3][N:2]([CH3:1])[C@H:6]1[N:7]2[CH3:15])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1
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Komponenten

5

Edukt 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 85760alpha-Methylbenzyl isocyanateHCID 88402553cis-(+/-)-1,2,3,3a,8,8a-Hexahydro-1,3a,8-trimethylpyrrolo [2,3-b]indol-4-ol

Produkt 1

HCID 53984692(+/-)-(3aR*,8aS*)-1,2,3,3a,8,8a-Hexahydro-1,3a,8-trimethylpyrrolo-[2,3-b]indol-4-yl (R)-(alpha-methylbenzyl)carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

cis-(±)-1,2,3,3a,8,8a-Hexahydro-1,3a,8-trimethylpyrrolo [2,3-b]indol-4-ol (2g) was dissolved in degassed THF (200 ml). DBU (0.8 ml) was added to the mixture followed by R-(+)-α-methylbenzyl isocyanate (2 g). The reaction was stirred at room temperature overnight under nitrogen. The solvent was evaporated under reduced pressure and the residue was purified using Prep 500 chromatography (4% MeOH/DCM) to yield 1.2 g of a solid. This material was combined with 600 mg of identically prepared material, which was found to be pure by thin layer analysis. The combined product was triturated with isopropyl ether and filtered to yield 1.8 g of (±)-(3aR*, 8aS*)-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo [2,3-b]indol-4-yl (R)-(α-methylbenzyl)carbamate, m.p. 151°-155° C.

Aufarbeitung

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-cb9d1bc99b9b4ab18c65744a87225d92
Quelldatensatz
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05726323

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