Lithium hydroxide, monohydrate → HCID 43810842, compound

HRID 218071Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:15][CH:14]2[CH2:16][CH:10]([CH2:11][CH:12]([C:17]([O:19]C)=[O:18])[CH2:13]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+]>C1COCC1.O.CO>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]2[CH2:16][CH:14]([CH2:13][CH:12]([C:17]([OH:19])=[O:18])[CH2:11]2)[CH2:15]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 30 °C

Procedure

Methyl 3-(tert-butoxycarbonyl)-3-azabicyclo[3.3.1]nonane-7-carboxylate (1.62 g, 5.72 mmol) was dissolved in a 2:1:2 mixture of THF/water/methanol (25 mL), and lithium hydroxide monohydrate (0.721 g, 17.2 mmol) was added. The reaction mixture was stirred at 30° C. for 16 h. The volatile solvents were removed by rotary evaporation, and the residue was acidified with 2 N hydrochloric acid and extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give 1.53 g (100% crude yield) of 3-(tert-butoxycarbonyl)-3-azabicyclo[3.3.1]nonane-7-carboxylic acid, as a colorless solid (1H NMR (CDCl3): δ 3.95-3.8 (m, 2H), 2.85-2.75 (m, 2H), 2.60-2.47 (m, 1H), 2.20-2.12 (m, 2H), 2.0-1.85 (m, 4H), 1.60-1.70 (m, 2H), 1.41 (s, 9H); (LC-MS (MH+): 270).

Workup

additionwas added
customThe volatile solvents were removed by rotary evaporation
extractionextracted with ethyl acetate (2×50 mL)
washThe combined organic extracts were washed with brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-600345eeaa53458598d101f4ac3d7bea
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08198296B2

Reaction notes

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