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

HRID 131185

반응식

HRID 131185 반응식
[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

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-b774b00d97c14d2faa38d525eb995df5
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384941B2

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