HCID 68466928, compound → HCID 68470095, compound

HRID 218062Notes

Reaction equation

HRID 218062 reaction equation
C(OC([N:8]1[CH2:15][CH:14]2[CH:10]([CH2:11][CH:12]([C:16](=[O:19])[CH2:17]Br)[CH2:13]2)[CH2:9]1)=O)(C)(C)C.[F:20][C:21]([F:26])([F:25])[C:22]([OH:24])=[O:23].C12C[CH:33]([C:35](=[O:39])[CH2:36]OC)CC1CNC2>C(O)(C)C>[F:20][C:21]([F:26])([F:25])[C:22]([OH:24])=[O:23].[CH:14]12[CH2:13][CH:12]([C:16](=[O:19])[CH2:17][O:39][CH:35]([CH3:36])[CH3:33])[CH2:11][CH:10]1[CH2:9][NH:8][CH2:15]2

Participants

4

Reactant 2

HCID 68466928HCID 68466928, compoundHCID 86643296HCID 86643296, compound

Product 1

HCID 68470095HCID 68470095, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

1-(3-Azabicyclo[3.3.0]oct-7-yl)-2-isopropoxy-1-ethanone trifluoroacetate was prepared from 1-(3-(tert-butoxycarbonyl)-3-azabicyclo[3.3.0]oct-7-yl)-2-bromo-1-ethanone (0.087 g, 0.27 mmol) and isopropanol, according to the procedure described above for the preparation of 1-(3-azabicyclo[3.3.0]oct-7-yl)-2-methoxy-1-ethanone trifluoroacetate, to give a mixture of cis and trans isomers (1H NMR (CD3OD, 300 MHz): δ 4.21 and 4.20 (s, 2H), 3.64 (heptet, J=6.1 Hz) 1H), 3.54-3.42 (m, 1H), 3.24-3.15 (m, 2H), 2.98-2.90 (m, 4H), 2.37-2.22 and 2.06-1.99 (m, 2H), 1.82-1.75 and 1.65-1.54 (m, 2H), 1.18 (d, J=6.1 Hz, 6H); MS (m/z): 212 (M+1)). This material exhibited Ki values at rat and human α4β2 of 427 nM and 261 nM respectively and did not pass HTS for α7.

Workup

  1. customto give
  2. additiona mixture of cis and trans isomers (1H NMR (CD3OD, 300 MHz): δ 4.21 and 4.20 (s, 2H), 3.64 (heptet, J=6.1 Hz) 1H), 3.54-3.42 (m, 1H), 3.24-3.15 (m, 2H), 2.98-2.90 (m, 4H), 2.37-2.22 and 2.06-1.99 (m, 2H), 1.82-1.75 and 1.65-1.54 (m, 2H), 1.18 (d, J=6.1 Hz, 6H)

Sources & evidence

ORD record
ord-33200ee879c546708e8f6224bc8155db
Source dataset
uspto-grants-2012_06
Patent number
US08198296B2

Reaction notes

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