Hydrochloric Acid → (1S,4S,6S)-4-(Hydroxymethyl)-3-azabicyclo[4.1.0]heptan-2-one

HRID 1094764Notes

Reaction equation

CC1(C)[N:6]2[C:7](=[O:12])[C@H:8]3[CH2:11][C@H:9]3[CH2:10][C@H:5]2[CH2:4][O:3]1.Cl>>[OH:3][CH2:4][C@@H:5]1[CH2:10][C@H:9]2[C@H:8]([CH2:11]2)[C:7](=[O:12])[NH:6]1

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 59396015HCID 59396015, compound

Product 1

HCID 55286764(1S,4S,6S)-4-(Hydroxymethyl)-3-azabicyclo[4.1.0]heptan-2-one

Conditions

Temperature: 40 °C

Procedure

(5aS,6aS,7aS)-3,3-dimethylhexahydro-5H-cyclopropa[d][1,3]oxazolo[3,4-a]pyridin-5-one D25 (3.56 g) was dissolved in HCl (25 ml, 150 mmol) (6 M in water) into a 250 ml-round bottomed flask and the mixture was stirred at 40° C.: after 4 hours the reaction was complete. The solvent was evaporated at reduced pressure using a rotavapor (bath temperature: 40° C.). The oily residue was stripped with toluene and the residue dried under high vacuum for 3 hours, obtaining the title compound D26 as white solid (2.843 g). UPLC (Acid IPQC): rt=0.31 minutes, peak observed: 142 (M+1). C7H11NO2 requires 141. 1H NMR (500 MHz, DMSO-d6) d ppm 0.56-0.68 (m, 1 H) 0.93-1.05 (m, 1 H) 1.30-1.39 (m, 1 H) 1.39-1.48 (m, 1 H) 1.57-1.67 (m, 1 H) 1.98-2.09 (m, 1 H) 3.17-3.29 (m, 2 H) 3.31-3.40 (m, 1 H) 6.89-7.13 (m, 1 H)

Workup

customThe solvent was evaporated at reduced pressure
customa rotavapor (bath temperature: 40° C.)
customthe residue dried under high vacuum for 3 hours

Sources & evidence

ORD record: ord-b25020e647104019ace0325b858be147
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08133908B2

Reaction notes

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