Lithium hydroxide, monohydrate → (1R,3S,4S,6R)-2-(tert-Butoxycarbonyl)-6-hydroxy-2-azabicyclo[2.2.1]heptane-3-carboxylic Acid

HRID 456732Notes

Reaction equation

[OH:1][C@H:2]1[C@H:7]2[CH2:8][C@H:4]([C@@H:5]([C:16]([O:18]CC)=[O:17])[N:6]2[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3]1.O.[OH-].[Li+]>O1CCOCC1.O>[C:12]([O:11][C:9]([N:6]1[C@H:5]([C:16]([OH:18])=[O:17])[C@H:4]2[CH2:8][C@@H:7]1[C@H:2]([OH:1])[CH2:3]2)=[O:10])([CH3:15])([CH3:13])[CH3:14]

Participants

Conditions

Temperature: 43 °C

Procedure

To a solution of 2-tert-butyl 3-ethyl (1R,3S,4S,6R)-6-hydroxy-2-azabicyclo[2.2.1]heptane-2,3-dicarboxylate obtained in Example 5-5 (249 mg) in dioxane (4.5 mL) and water (1.5 mL), was added lithium hydroxide monohydrate (110 mg). The mixture was stirred at 43° C. for 12 hrs and then 60° C. for 3 hrs. The resulting mixture was evaporated in vacuo. 1N Hydrochloric acid (2.7 mL) was added to the residue, and the mixture was extracted with ethyl acetate. The combined organic phase was washed with brine, dried over NaSO4, and evaporated in vacuo. The residue was triturated with ether to give the target compound (164 mg) as a solid.

Workup

wait60° C. for 3 hrs
customThe resulting mixture was evaporated in vacuo
addition1N Hydrochloric acid (2.7 mL) was added to the residue
extractionthe mixture was extracted with ethyl acetate
washThe combined organic phase was washed with brine
dry with materialdried over NaSO4
customevaporated in vacuo
customThe residue was triturated with ether

Sources & evidence

ORD record: ord-effca8c0485b466c8840c34a2fc90763
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07186731B2

Reaction notes

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