Hydrochloric Acid → 1-(2,5-Diaza-bicyclo[2.2.1]hept-2-yl)-2-hydroxy-ethanone hydrochloride

HRID 384513Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH:12]2[CH2:14][CH:9]1[CH2:10][N:11]2[C:15](=[O:21])[CH2:16][O:17]C(=O)C)=O)(C)(C)C.[ClH:22]>C(O)(C)C>[ClH:22].[CH:12]12[CH2:14][CH:9]([NH:8][CH2:13]1)[CH2:10][N:11]2[C:15](=[O:21])[CH2:16][OH:17]

Participants

Conditions

Temperature: 51 °C

Procedure

To a slurry of 5-(2-acetoxy-acetyl)-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (1.2 g, 4 mmol) in isopropanol (16 mL) was quickly added 5 M HCl in isopropanyl (3.2 mL, 16 mmol). The mixture was warmed to 51° C. and stirred for 20 h. It was then concentrated to provide the title compound in 97 wt % purity (767 mg, 96%). MS (ESI): mass calcd. for C7H12N2O2, 156.1; m/z found, 157.1 [M+H]+. 1H NMR (600 MHz, DMSO-d6): 9.9-9.2 (m, 2H), 4.73-4.71 (m, 1H), 4.42-4.37 (m, 1H), 4.1-3.9 (m, 2H), 3.79-3.77 (m, 0.5H), 3.55-3.48 (m, 1H), 3.37-3.35 (m, 0.5H), 3.25-3.07 (m, 2H), 2.00-1.82 (m, 2H).

Workup

concentrationIt was then concentrated

Sources & evidence

ORD record: ord-93cd72830a4a416e8263742638ed2d31
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367719B2

Reaction notes

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