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

HRID 1271346Notes

Reaction equation

HRID 1271346 reaction equation
[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]

Participants

4

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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) δ 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).

Workup

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

Sources & evidence

ORD record
ord-a8f9d5a560bc45aaafd9e76bfef0e043
Source dataset
uspto-grants-2007_04
Patent number
US07205300B2

Reaction notes

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