Lithium Hydroxide → 2-[(tert-Butoxycarbonyl)amino]-2-methylcyclopentane-1-carboxylic acid

HRID 1750513Notes

Reaction equation

[OH-].[Li+].[C:3]([O:7][C:8]([NH:10][C:11]1([CH3:20])[CH2:15][CH2:14][CH2:13][CH:12]1[C:16]([O:18]C)=[O:17])=[O:9])([CH3:6])([CH3:5])[CH3:4]>C1COCC1.O>[C:3]([O:7][C:8]([NH:10][C:11]1([CH3:20])[CH2:15][CH2:14][CH2:13][CH:12]1[C:16]([OH:18])=[O:17])=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

Conditions

Temperature: 50 °C

Procedure

Lithium hydroxide (23.50 g, 981 mmol) was added to a solution of methyl 2-{ [(tert-butoxy)carbonyl]amino}-2-methylcyclopentane-1-carboxylate (50.51 g, 196 mmol) in THF (300 ml) and water (150 ml). The reaction was heated at 50° C. for 18 hours and then to 60° C. for 18 hours. The reaction was concentrated in vacuo and then acidified to pH 7 with concentrated HCl and then to pH 3 with 2 M HCl (aq). The organics were extracted with ethyl acetate (3×300 ml) and the combined organics were washed with brine (50 ml), dried over magnesium sulfate and concentrated in vacuo to afford the title compound which was used without further purification.

Workup

concentrationThe reaction was concentrated in vacuo
extractionThe organics were extracted with ethyl acetate (3×300 ml)
washthe combined organics were washed with brine (50 ml)
dry with materialdried over magnesium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-e64c5a1d17e94237be851bde0221560c
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156829B2

Reaction notes

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