Sodium cyanoborohydride → N-[2-(4-Methoxycarbonylmethylphenoxy)-1(S)-methylethyl]-2(S)-t-butyldimehylsilyloxy-2-phenylethanamine

HRID 1901212Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1901212
[Si:1]([O:8][C@@H:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH:10]=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[NH2:18][C@@H:19]([CH3:33])[CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29]([O:31][CH3:32])=[O:30])=[CH:24][CH:23]=1.C([BH3-])#N.[Na+]>CO>[CH3:32][O:31][C:29]([CH2:28][C:25]1[CH:26]=[CH:27][C:22]([O:21][CH2:20][C@@H:19]([NH:18][CH2:10][C@@H:9]([O:8][Si:1]([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3])[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH3:33])=[CH:23][CH:24]=1)=[O:30]

Komponenten

5

Edukt 3

HCID 5003444Sodium cyanoborohydrideHCID 11075902(S)-alpha-(t-Butyldimethylsilyloxy)-alpha-phenylacetaldehydeHCID 22867084Methyl 4-[2(S)-amino-1-propoxy]phenylacetate

Produkt 1

HCID 22867088N-[2-(4-Methoxycarbonylmethylphenoxy)-1(S)-methylethyl]-2(S)-t-butyldimehylsilyloxy-2-phenylethanamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Following a procedure similar to that described in Preparation 29, but using 1.5 g of (S)-α-(t-butyldimethylsilyloxy)-α-phenylacetaldehyde (prepared as described in Preparation 26), 1.1 g of methyl 4-[2(S)-amino-1-propoxy]phenylacetate (prepared as described in Preparation 28), 10 ml of absolute methanol and 950 mg of sodium cyanoborohydride, the title compound was obtained.

Aufarbeitung

  1. customthat described in Preparation 29

Quellen und Nachweise

ORD-Eintrag
ord-a46b03fc76b142e692bfb57c3df94256
Quelldatensatz
uspto-grants-1996_11
Patentnummer
US05576340

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