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1,1-Dichloroethane → (4s,5r)-5-[3,5-Bis(trifluoromethyl)phenyl]-3-[2-[(diethylamino)methyl]-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one

HRID 505281
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HRID 505281 반응식
[F:1][C:2]([F:34])([F:33])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[CH:24]C=3C=O)[C@H]2C)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[NH:35]([CH2:38][CH3:39])[CH2:36][CH3:37].[BH-](OC(C)=O)(OC(C)=O)O[C:42]([CH3:44])=O.[Na+].Cl[CH:55](Cl)[CH3:56]>CCOC(C)=O>[F:1][C:2]([F:33])([F:34])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[CH:24][C:37]=3[CH2:36][N:35]([CH2:42][CH3:44])[CH2:38][CH3:39])[C@H:55]2[CH3:56])[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1
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반응물 4

HCID 63651,1-DichloroethaneHCID 8021DiethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 576178812-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4-(trifluoromethyl)benzaldehyde

생성물 1

HCID 24896004(4s,5r)-5-[3,5-Bis(trifluoromethyl)phenyl]-3-[2-[(diethylamino)methyl]-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4-(trifluoromethyl)benzaldehyde (14.5 mg, 0.0291 mmol) in dichloroethane (300 μL) was added HNEt2 (4.6 μL, 0.0436 mmol), and NaBH(OAc)3 (9.2 mg, 0.0436 mmol). The reaction was stirred at room temperature for 18 hours and then diluted with EtOAc (10 mL) and washed with brine (5 mL). The organic layer was dried over Na2SO4, filtered, and concentrated. Purification of the residue by PTLC (50% EtOAc/hexanes) afforded (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-[(diethylamino)methyl]-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one. Rf=0.57 (50% EtOAc/hexanes). LCMS=557.2 (M+1)+. 1H NMR (CDCl3, 500 MHz) δ 7.92 (s, 1H), 7.82 (s, 2H), 7.55-7.52 (m, 3H), 5.76 (d, J=8.0 Hz, 1H), 5.03 (d, J=16.1 Hz, 1H), 4.60 (d, J=16.1 Hz, 1H), 4.05-4.03 (m, 1H), 3.73 (d, J=13.5 Hz, 1H), 3.57 (d, J=13.7 Hz, 1H), 2.75-2.56 (m, 4H), 1.04 (bs, 6H), 0.80 (d, J=6.4 Hz, 3H).

후처리

  1. washwashed with brine (5 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification of the residue by PTLC (50% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-d0e9ea6bb19c4ed9a6dda3eef0e7310b
출처 데이터셋
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07781426B2

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