Methanol → HCID 50898815, compound

HRID 601953Notes

Reaction equation

HRID 601953 reaction equation
C([O:3][C:4]([C:6]1[NH:13][C:12]2[C@@H:11]3[CH2:14][C@@H:10]3[CH2:9][C:8]=2[CH:7]=1)=[O:5])C.[OH-].[Li+].CO>C1COCC1>[CH2:14]1[C@@H:10]2[CH2:9][C:8]3[CH:7]=[C:6]([C:4]([OH:5])=[O:3])[NH:13][C:12]=3[C@H:11]12

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 131728745HCID 131728745, compound

Product 1

HCID 50898815HCID 50898815, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was synthesized from (1aR,5aR)-1a,2,5,5a-tetrahydro-1H-2-aza-cyclopropa[α]pentalene-3-carboxylic acid ethyl ester (115 mg, 0.6 mmol) and lithium hydroxide (252 mg, 6.0 mmol in 5 mL water) according to General Procedure 7. A 1:1 mixture of methanol (MeOH) and THF (10 mL) was used. The resulting product was purified by chromatography eluting with heptane-EtOAc, gradient 0 to 50% EtOAc. 27 mg. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.31-0.39 (m, 1H), 1.06-1.16 (m, 1H), 2.04-2.19 (m, 2H), 2.63 (d, J=15.67 Hz, 1H), 2.84 (dd, J=15.62, 6.35 Hz, 1H), 6.73 (s, 1H), 8.97 (br. s, 1H). LCMS m/e 164 (M+H). Purity>85% (HPLC).

Workup

  1. customThe resulting product was purified by chromatography
  2. washeluting with heptane-EtOAc, gradient 0 to 50% EtOAc

Sources & evidence

ORD record
ord-73e8ed3ce1914980b96f1d83c50670bc
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

Loading…