Water → 2-(Tert-butoxycarbonyl)-2-azatricyclo[3.3.1.13,7]decane-5-carboxylic acid

HRID 623982Notes

Reaction equation

[CH:1]12[CH2:10][C:5]3([C:11]([O:13]C)=[O:12])[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[N:2]1[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:8]2.C1COCC1.O.[Li+].[OH-]>CO>[C:18]([O:17][C:15]([N:2]1[CH:3]2[CH2:9][CH:7]3[CH2:6][C:5]([C:11]([OH:13])=[O:12])([CH2:10][CH:1]1[CH2:8]3)[CH2:4]2)=[O:16])([CH3:21])([CH3:19])[CH3:20]

Participants

Conditions

Temperature: 0 °C

Procedure

To a 0° C. cooled stirred solution of 2-tert-butyl 5-methyl 2-azatricyclo[3.3.1.13,7]decane-2,5-dicarboxylate, intermediate-9 (0.16 g, 0.5 mmol) dissolved in methanol (3 ml), THF (1 ml) and water (1 ml), LiOH (50 mg, 2 mmol) was added and the resulting reaction mass was stirred at room temperature for 6 hrs. Upon completion of the reaction (reaction monitored by TLC), the solvent present in the reaction mixture was completely removed under vacuum and the crude residue was acidified with saturated citric acid solution and extracted with ethyl acetate (3×15 ml). The organic layer was then washed with brine solution and dried over sodium sulfate and was finally concentrated under vacuum to get intermediate-10 as an oily mass, 0.16 g (95%).

Workup

customthe resulting reaction mass
customUpon completion of the reaction (reaction monitored by TLC)
customthe solvent present in the reaction mixture was completely removed under vacuum
extractionextracted with ethyl acetate (3×15 ml)
washThe organic layer was then washed with brine solution
dry with materialdried over sodium sulfate
concentrationwas finally concentrated under vacuum
customto get intermediate-10 as an oily mass, 0.16 g (95%)

Sources & evidence

ORD record: ord-39bbc7b12f444aab8ea0ad1ba00415ba
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09303016B2

Reaction notes

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