Diethyl Ether → [(1S,2S,5R)-2-aminomethyl-7-methyl-3-aza-bicyclo[3.3.0]oct-3-yl]-(2-methyl-5-m-tolyl-thiazol-4-yl)-methanone

HRID 425802Notes

Reaction equation

HRID 425802 reaction equation
FC(F)(F)C([NH:5][CH2:6][C@H:7]1[N:14]([C:15]([C:17]2[N:18]=[C:19]([CH3:29])[S:20][C:21]=2[C:22]2[CH:23]=[C:24]([CH3:28])[CH:25]=[CH:26][CH:27]=2)=[O:16])[CH2:13][C@H:12]2[C@@H:8]1[CH2:9][CH:10]([CH3:30])[CH2:11]2)=O.C([O-])([O-])=O.[K+].[K+].CCOCC>CO>[NH2:5][CH2:6][C@H:7]1[N:14]([C:15]([C:17]2[N:18]=[C:19]([CH3:29])[S:20][C:21]=2[C:22]2[CH:23]=[C:24]([CH3:28])[CH:25]=[CH:26][CH:27]=2)=[O:16])[CH2:13][C@H:12]2[C@@H:8]1[CH2:9][CH:10]([CH3:30])[CH2:11]2

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 866435452,2,2-trifluoro-N-[(1S,2S,5R)-3-(2-methyl-5-m-tolyl-thiazole-4-carbonyl)-7-methyl-3-aza-bicyclo[3.3.0]oct-2-ylmethyl]-acetamide

Product 1

HCID 59411601[(1S,2S,5R)-2-aminomethyl-7-methyl-3-aza-bicyclo[3.3.0]oct-3-yl]-(2-methyl-5-m-tolyl-thiazol-4-yl)-methanone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2,2,2-trifluoro-N-[(1S,2S,5R)-3-(2-methyl-5-m-tolyl-thiazole-4-carbonyl)-7-methyl-3-aza-bicyclo[3.3.0]oct-2-ylmethyl]-acetamide (1.96 g) was dissolved in MeOH (20 mL) and a sat. aq. K2CO3 solution was added (20 mL). The reaction mixture was stirred overnight at RT. Ether was added to the reaction mixture and the org. layer was extracted with aq. HCl (25%) and aq. HCl (1M). The org. phase was discarded and the aq. layers were basified with aq. 30% NaOH and then extracted with DCM. The combined org. extracts were washed with a sat. aq. NaHCO3 solution, dried over anh. MgSO4, filtered and concentrated to yield the title compound as a light orange oil which was used without further purification.

Workup

  1. extractionlayer was extracted with aq. HCl (25%) and aq. HCl (1M)
  2. extractionextracted with DCM
  3. washextracts were washed with a sat. aq. NaHCO3 solution
  4. dry with materialdried over anh. MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-411e7770552146b6a202d07c7912e894
Source dataset
uspto-grants-2012_01
Patent number
US08106215B2

Reaction notes

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