2-Bromoethanol → Methyl(3R,4R)-4-{[(benzyloxy)carbonyl]amino}-1-(2-hydroxyethyl)piperidine-3-carboxylate

HRID 1644318Notizen

Reaktionsgleichung

C(OC(N[C@@H]1CCNC[C@@H]1C(OC)=O)=O)C1C=CC=CC=1.C(N(CC)C(C)C)(C)C.BrCCO.[CH2:35]([O:42][C:43]([NH:45][C@@H:46]1[CH2:51][CH2:50][N:49]([CH2:52][CH2:53][OH:54])[CH2:48][C@@H:47]1[C:55]([O:57][CH3:58])=[O:56])=[O:44])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>>[CH2:35]([O:42][C:43]([NH:45][C@@H:46]1[CH2:51][CH2:50][N:49]([CH2:52][CH2:53][OH:54])[CH2:48][C@H:47]1[C:55]([O:57][CH3:58])=[O:56])=[O:44])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Komponenten

Edukt 4

HCID 108982-Bromoethanol

HCID 81531Diisopropylethylamine

HCID 58999552methyl (3S,4R)-4-{[(benzyloxy)carbonyl]amino}piperidine-3-carboxylate

HCID 66774341Methyl(3S,4R)-4-{[(benzyloxy)carbonyl]amino}-1-(2-hydroxyethyl)piperidine-3-carboxylate

Produkt 1

HCID 66775250Methyl(3R,4R)-4-{[(benzyloxy)carbonyl]amino}-1-(2-hydroxyethyl)piperidine-3-carboxylateAusbeute 60 %

Versuchsvorschrift

Methyl(3S,4R)-4-{[(benzyloxy)carbonyl]amino}piperidine-3-carboxylate (WO 2005/066176) (2.0 g, 6.84 mmol), N,N-diisopropylethylamine (1.8 mL, 10.26 mmol) and 2-bromoethanol (0.63 mL, 8.9 mmol) were reacted as described for Intermediate 37 to give 1.38 g (60%) of the product as a colorless oil.

Quellen und Nachweise

ORD-Eintrag: ord-a93e1beab31e45d18ca2c0cc35b245d6
Quelldatensatz: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08124602B2

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