Glyceraldehyde → (2R,3R,4R)-3,4-dibenzyloxy-2-benzyloxymethyl-1-(2,3-dihydroxyprop-1-yl)pyrrolidine

HRID 1280807Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1280807
C([O:8][C@H:9]1[C@H:13]([O:14]CC2C=CC=CC=2)CN(CCCC)[C@@H:10]1COCC1C=CC=CC=1)C1C=CC=CC=1.[CH2:35]([O:42][C@H:43]1[C@H:47]([O:48][CH2:49][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[CH2:46][NH:45][C@@H:44]1[CH2:56][O:57][CH2:58][C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.O=CC(CO)O.C([BH3-])#N.[Na+]>CO>[CH2:35]([O:42][C@H:43]1[C@H:47]([O:48][CH2:49][C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=2)[CH2:46][N:45]([CH2:10][CH:9]([OH:8])[CH2:13][OH:14])[C@@H:44]1[CH2:56][O:57][CH2:58][C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Komponenten

6

Edukt 4

HCID 751GlyceraldehydeHCID 5003444Sodium cyanoborohydrideHCID 22842874(2R,3R,4R)-3,4-dibenzyloxy-2-benzyloxymethylpyrrolidine2×HCID 53802070(2R,3R,4R)-3,4-dibenzyloxy-2-benzyloxymethyl-1-butylpyrrolidine

Produkt 1

HCID 54393635(2R,3R,4R)-3,4-dibenzyloxy-2-benzyloxymethyl-1-(2,3-dihydroxyprop-1-yl)pyrrolidineAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

The title compound was synthesized as described for compound 10 using (2R,3R,4R)-3,4-dibenzyloxy-2-benzyloxymethylpyrrolidine (Compound 1) (0.5 g, 1.2 mmol), methanol (30 ml), glyceraldehyde (0.134 g, 1.5 mmol) and sodium cyanoborohydride (0.094 g, 1.5 mmol). Purification of the crude product on silica gel (Eluent: Ethyl acetate) afforded (2R,3R,4R)-3,4-dibenzyloxy-2-benzyloxymethyl-1-(2,3-dihydroxyprop-1-yl)pyrrolidine (0.424 g, yield: 72%) as an oil.

Aufarbeitung

  1. customThe title compound was synthesized
  2. customPurification of the crude product on silica gel (Eluent: Ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-fd1226dda6004ccc8fbddd8f7288a53b
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06451836B1

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