Lithium Hydroxide → HCID 59180066, compound

HRID 601867Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][CH:21]=1)[CH2:6][CH:7]1[C:14]2[CH:13]=[C:12]([C:15]([O:17]C)=[O:16])[NH:11][C:10]=2[CH2:9][CH2:8]1)#[N:2].[Li+].[OH-:23]>C1COCC1.CO.O>[C:1]([C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][CH:21]=1)[CH2:6][CH:7]1[C:14]2[CH:13]=[C:12]([C:15]([OH:17])=[O:16])[NH:11][C:10]=2[CH2:9][CH2:8]1)(=[O:23])[NH2:2].[C:1]([C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][CH:21]=1)[CH2:6][CH:7]1[C:14]2[CH:13]=[C:12]([C:15]([OH:17])=[O:16])[NH:11][C:10]=2[CH2:9][CH2:8]1)#[N:2]

Participants

Conditions

Temperature: 40 °C

Procedure

Methyl 4-(3-cyanobenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.065 g, 0.23 mmol) was dissolved in THF (1 mL) and MeOH (1 mL). Then LiOH (0.097 g, 2.31 mmol) in H2O (1 mL) was added and the reaction stirred at 40° C. for 16 h. The solvent was removed under reduced pressure, and the residue re-dissolved in about 5 mL H2O and acidified to pH 2-3 with 1 N HCl. The product was filtered off, and then dissolved in DMSO (about 15 mg/mL) and purified by reverse phase HPLC, eluting with a gradient of 40-80% MeOH: water (with 0.1% formic acid) to afford both 4-(3-carbamoylbenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acid (77) and 4-(3-cyanobenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acid (75).

Workup

customThe solvent was removed under reduced pressure
dissolutionthe residue re-dissolved in about 5 mL H2O
filtrationThe product was filtered off
dissolutiondissolved in DMSO (about 15 mg/mL)
custompurified by reverse phase HPLC
washeluting with a gradient of 40-80% MeOH

Sources & evidence

ORD record: ord-2e108c15e738450abf0e63347d60f483
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902252B2

Reaction notes

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