Trifluoroacetic acid → Phenylmethyl {[(3S,4R)-4-hydroxy-3-pyrrolidinyl]methyl}carbamate

HRID 657004Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 657004
[OH:1][C@@H:2]1[C@H:6]([CH2:7][NH:8][C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:5][N:4](C(OC(C)(C)C)=O)[CH2:3]1.O[C@H]1[C@@H](CNC(OCC2C=CC=CC=2)=O)CN(C(OC(C)(C)C)=O)C1.FC(F)(F)C(O)=O.CC[NH+](CC)CC.CC[NH+](CC)CC.C([O-])([O-])=O>C(Cl)Cl.CO>[OH:1][C@H:2]1[CH2:3][NH:4][CH2:5][C@H:6]1[CH2:7][NH:8][C:9](=[O:10])[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

7

Edukt 4

HCID 6422Trifluoroacetic acidHCID 15264167Carbonic acid--N,N-diethylethanamine (1/2)HCID 59254350rac-tert-butyl (3R,4R)-3-({[(benzyloxy)carbonyl]amino}methyl)-4-hydroxypyrrolidine-1-carboxylateHCID 592543621,1-dimethylethyl (3R,4R)-3-hydroxy-4-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-pyrrolidinecarboxylate

Produkt 1

HCID 86616784Phenylmethyl {[(3S,4R)-4-hydroxy-3-pyrrolidinyl]methyl}carbamateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 1,1-dimethylethyl (3R,4R)-3-hydroxy-4-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-pyrrolidinecarboxylate (for a synthesis see WO2006002047, Preparation 24(c) (±)-1,1-dimethylethyl cis-3-hydroxy-4-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-pyrrolidinecarboxylate E2 isomer) (2 g, 5.7 mmol) in DCM (50 ml) was added trifluoracetic acid (50 mL) and stirred for 2 h. The reaction mixture was concentrated and placed under high-vac for 3 h. To the TFA salt dissolved in 100 ml of 10:1 CHCl3:MeOH was added MP-carbonate resin (8 g; 22.8 mmol) and stirred overnight. The reaction mixture was filtered and concentrated to provide the title compound as a pale yellow oil (1.4 g; 100%).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. customhigh-vac for 3 h
  3. dissolutionTo the TFA salt dissolved in 100 ml of 10:1 CHCl3
  4. stirringstirred overnight
  5. filtrationThe reaction mixture was filtered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c369e84b488d4732a9fca5b03667e7ed
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071592B2

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