Sodium Bicarbonate → 2,2,2-trifluoro-1-(7-hydroxy-4,5-dihydro-1H-1,5-methanobenzo[d]azepin-3(2H)-yl)ethanone

HRID 457442노트

반응식

HRID 457442 반응식
[F:1][C:2]([F:22])([F:21])[C:3]([N:5]1[CH2:15][CH:14]2[CH2:16][CH:7]([C:8]3[CH:9]=[CH:10][C:11]([O:17]C(=O)C)=[CH:12][C:13]=32)[CH2:6]1)=[O:4].C([O-])(O)=O.[Na+]>CO>[F:22][C:2]([F:1])([F:21])[C:3]([N:5]1[CH2:15][CH:14]2[CH2:16][CH:7]([C:8]3[CH:9]=[CH:10][C:11]([OH:17])=[CH:12][C:13]=32)[CH2:6]1)=[O:4]

참가 물질

4

반응물 2

HCID 516892Sodium BicarbonateHCID 54458016Acetic acid 10-trifluoroacetyl-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-4-yl ester

생성물 1

HCID 218647432,2,2-trifluoro-1-(7-hydroxy-4,5-dihydro-1H-1,5-methanobenzo[d]azepin-3(2H)-yl)ethanone

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Acetic acid 10-trifluoroacetyl-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-4-yl ester (900 mg, 2.87 mmol) was stirred in methanol (20 mL) and saturated aqueous NaHCO3 solution (15 mL) for 48 hours. The mixture was concentrated, diluted with H2O and extracted with CH2Cl2 (3×20 mL) then dried through a cotton plug. Chromatography on Silica gel provided pure product (420 mg, 54%). (TLC 5% methanol/CH2Cl2 Rf 0.44). 1H NMR (400 MHz, CDCl3)7.05 (m, 1H), 6.70 (m, 1H), 6.62 (m, 1H), 4.32 (m, 1H), 3.84 (m, 1H), 3.48 (m, 1H), 3.21 (br s, 1H), 3.16 (br s, 1H), 3.09 (m, 1H), 2.38 (m, 1H), 1.97 (d, J=11.0 Hz, 1H).

후처리

  1. concentrationThe mixture was concentrated
  2. additiondiluted with H2O
  3. extractionextracted with CH2Cl2 (3×20 mL)
  4. customthen dried through a cotton plug

출처 및 근거

ORD 기록
ord-f69afd8e83574eceb4d1789b0e5ce8f7
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07186870B2

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