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

HRID 131185

反応式

HRID 131185 の反応式
[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

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-b774b00d97c14d2faa38d525eb995df5
出典データセット
uspto-grants-2008_06
特許番号
US07384941B2

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