Lithium Hydroxide → HCID 49850051, compound

HRID 601950Notes

Reaction equation

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

Participants

Reactant 2

HCID 3939Lithium Hydroxide

HCID 59180171HCID 59180171, compound

Product 1

HCID 49850051HCID 49850051, compound

Procedure

The title compound was synthesized from ±(1aS,5aS)-1a,4,5,5a-tetrahydro-1H-4-aza-cyclopropa[α]pentalene-3-carboxylic acid ethyl ester (65 mg, 0.34 mmol) and lithium hydroxide (143 mg, 3.40 mmol in 5 mL water), according to General Procedure 7. The resulting product was purified by crystallization from Et2O. 35 mg. 1H NMR (METHANOL-d4) δ: 6.61 (s, 1H), 2.90 (dd, J=16.7, 6.3 Hz, 1H), 2.69 (d, J=16.7 Hz, 1H), 1.88-2.02 (m, 2H), 0.95-1.04 (m, 1H), 0.07 (q, J=4.0 Hz, 1H). LCMS m/e 164 (M+H). Purity ˜100% (HPLC).

Workup

customThe resulting product was purified by crystallization from Et2O

Sources & evidence

ORD record: ord-db037f37193b4566b5ee69f9dfeb9840
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902252B2

Reaction notes

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