Trifluoroacetic acid → (R)-Phenyl{(2S)-4-[(1R)-1-phenylethyl]morpholin-2-yl}methanol

HRID 131185

Reaktionsgleichung

Reaktionsgleichung von HRID 131185
[C:1]1([C:7]([C@H:9]2[O:14][CH2:13][CH2:12][N:11]([C@@H:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH3:16])[CH2:10]2)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1([SiH](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.B(F)(F)F.CCOCC.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[C:1]1([C@H:7]([C@H:9]2[O:14][CH2:13][CH2:12][N:11]([C@@H:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH3:16])[CH2:10]2)[OH:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

7

Edukt 5

HCID 6422Trifluoroacetic acidHCID 8000Boron trifluoride etherateHCID 69922TriphenylsilaneHCID 516892Sodium BicarbonateHCID 59732184Phenyl{(2S)-4-[(1R)-1-phenylethyl]morpholin-2-yl}methanone

Produkt 1

HCID 59732175(R)-Phenyl{(2S)-4-[(1R)-1-phenylethyl]morpholin-2-yl}methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 48a (0.08 g, 0.26 mmol) and triphenylsilane (0.34 g, 1.31 mmol) in dichloromethane (4 ml) cooled to 0° C. was added boron trifluoride etherate (0.09 g, 0.66 mmol) followed by trifluoroacetic acid (0.36 ml, 63 mmol). The reaction mixture was allowed to warm to room temperature and diluted after three hours with dichloromethane (20 ml) and neutralised with aqueous sodium bicarbonate. The organic phase was dried over magnesium sulphate, filtered and evaporated to give the required product. This was purified as its hydrochloric acid salt crystallising from isopropanol and diethyl ether (0.05 g, 69%%); MW 297.4; C19H23NO2; 1H NMR (CDCl3) on free base 7.08-7.29 (10H, m), 4.78 (1H, d), 3.90-4.00 (1H, m), 3.57-3.68 (2H, m), 3.33 (1H, q), 2.53-2.64 (1H, m), 2.37-2.47 (1H, m), 2.09-2.26 (2H, m), 1.29 (3H, d). m/z [M+H]+ 298.

Aufarbeitung

  1. dry with materialThe organic phase was dried over magnesium sulphate
  2. filtrationfiltered
  3. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-b774b00d97c14d2faa38d525eb995df5
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384941B2

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