Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → HCID 44406489, compound

HRID 458136Notes

Reaction equation

HRID 458136 reaction equation
[C:1]1([N:7]2[C:11]3([CH2:16][CH2:15][N:14]([C@@H:17]4[CH2:22][CH2:21][CH2:20][CH2:19][C@@H:18]4[C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH2:13][CH2:12]3)[C:10](=[O:29])[NH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O>CO>[C:1]1([N:7]2[C:11]3([CH2:16][CH2:15][N:14]([C@H:17]4[CH2:22][CH2:21][CH2:20][CH2:19][C@H:18]4[C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH2:13][CH2:12]3)[C:10](=[O:29])[NH:9][CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 11406629HCID 11406629, compound

Product 1

HCID 44406489HCID 44406489, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Elucidation of absolute stereochemistry: To a solution of 24 mg (cis)-1-phenyl-8-(2-phenyl-cyclohexyl)-1,3,8-triaza-spiro[4.5]decan-4-one (Example 2) in methanol were added 14 mg 1R-(−)-camphorsulfonic acid and the solution stirred for 10 min. at ambient temperature. The resulting salt slurry was evaporated and the residue crystallized from ethyl acetate. With the single crystal X-ray structural analysis of the 1R-(−)-camphorsulfonic acid salt the absolute configuration at the cyclohexane ring was established as 1S and 2S.

Workup

  1. customThe resulting salt slurry was evaporated
  2. customthe residue crystallized from ethyl acetate

Sources & evidence

ORD record
ord-9750aafb66924a89b327918f85d10812
Source dataset
uspto-grants-2007_03
Patent number
US07189850B2

Reaction notes

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