Methanol → HCID 178421817, compound

HRID 1295071Notes

Reaction equation

HRID 1295071 reaction equation
C([O:3][C:4]([C:6]1[NH:13][N:12]=[C:11]2[C:7]=1[CH2:8][CH:9]1[C:14]([CH3:16])([CH3:15])[CH:10]12)=[O:5])C.CO.[OH-].[Li+]>C1COCC1>[CH3:15][C:14]1([CH3:16])[CH:9]2[CH2:8][C:7]3[C:11]([CH:10]12)=[N:12][NH:13][C:6]=3[C:4]([OH:5])=[O:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 178470406HCID 178470406, compound

Product 1

HCID 178421817HCID 178421817, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(±)-1,1-Dimethyl-1a,3,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carboxylic acid ethyl ester (0.0390 g, 0.177 mmol) was stirred for 18 hours at room temperature in a solution of 1:5:1 methanol:THF:1M aqueous lithium hydroxide (14 mL). Solvent was removed under reduced pressure, the residue was taken up in 1M aqueous hydrochloric acid (5 mL) and extracted into ethyl acetate (40 mL). Solvent was removed under reduced pressure and the residue purified by preparative HPLC to give a white solid. m/z (ES+): 215 [M+Na]+, 193 [M+H]+, 175 [M−OH]+; 1H NMR (CD3CN): δ 2.91 (dd, 1H, J1=17.4, J2=6.8), 2.66 (d, 1H, J=17.4), 2.11 (dd, 1H, J1=6.3, J2=1.2), 2.05–1.95 (m, 1H), 1.19 (s, 3H, exo-CH3), 0.77 (d, 3H, J=2.0, endo-CH3).

Workup

  1. customSolvent was removed under reduced pressure
  2. extractionextracted into ethyl acetate (40 mL)
  3. customSolvent was removed under reduced pressure
  4. customthe residue purified by preparative HPLC
  5. customto give a white solid

Sources & evidence

ORD record
ord-e9ff01c0df504974958e27c9bc3eeaaf
Source dataset
uspto-grants-2007_07
Patent number
US07241792B2

Reaction notes

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