Trityl chloride → (2R,4R)-4-Hydroxy-1-trityl-pyrrolidine-2-carboxylic acid methyl ester

HRID 1796299

Reaktionsgleichung

Reaktionsgleichung von HRID 1796299
[CH3:1][O:2][C:3]([C@H:5]1[CH2:9][C@@H:8]([OH:10])[CH2:7][NH:6]1)=[O:4].C(N(CC)CC)C.[C:18]1([C:24](Cl)([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]([C@H:5]1[CH2:9][C@@H:8]([OH:10])[CH2:7][N:6]1[C:24]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)=[O:4]

Komponenten

5

Edukt 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 7020012(2R,4R)-methyl 4-hydroxypyrrolidine-2-carboxylate

Produkt 1

HCID 68685802(2R,4R)-4-Hydroxy-1-trityl-pyrrolidine-2-carboxylic acid methyl esterAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

Into a solution of 1 (10 g, 55 mmol) in anhydrous CHCl3 (100 mL) was added triethylamine (19 mL, 138 mmol) and triphenylmethyl chloride (14.5 g, 52 mmol). The mixture was stirred at RT for 3 d before concentrating and redissolving in EtOAc. The solution was washed sequentially with 10% aq. citric acid, water, and brine before drying over MgSO4 and concentrating under reduced pressure to give 2 (20 g, 100%) as a yellow solid.

Aufarbeitung

  1. concentrationbefore concentrating
  2. dissolutionredissolving in EtOAc
  3. washThe solution was washed sequentially with 10% aq. citric acid, water, and brine
  4. dry with materialbefore drying over MgSO4
  5. concentrationconcentrating under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-03d797ef84384cc3a42572b877c4cb58
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07030141B2

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