Hydrochloric Acid → (R)-1-(tert-butoxycarbonyl)-3,3-dimethyl-1,3-azasilolidine-5-carboxylic acid

HRID 527735Notes

Reaction equation

HRID 527735 reaction equation
[CH3:1][Si:2]1([CH3:18])[CH2:6][C@@H:5]([C:7]([O:9]C)=[O:8])[N:4]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:3]1.O.[OH-].[Li+].Cl>C1COCC1.CO.O>[C:14]([O:13][C:11]([N:4]1[C@H:5]([C:7]([OH:9])=[O:8])[CH2:6][Si:2]([CH3:18])([CH3:1])[CH2:3]1)=[O:12])([CH3:17])([CH3:16])[CH3:15]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 10730990HCID 10730990, compound

Product 1

HCID 10825193(R)-1-(tert-butoxycarbonyl)-3,3-dimethyl-1,3-azasilolidine-5-carboxylic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-1-tert-butyl 5-methyl 3,3-dimethyl-1,3-azasilolidine-1,5-dicarboxylate (3.1 g, 11.3 mmol, Eur. J. Org. Chem., 807-811 (2000)) in THF (10 mL) and MeOH (15 mL) was added a solution of lithium hydroxide monohydrate (2.9 g, 68 mmol) in water (15 mL). The resulting reaction mixture was stirred at rt for 4 h and the pH was adjusted to 1 using 1N HCl. The resulting aqueous layer was extracted with ethyl ether (2×). The organic solution was dried over MgSO4 and concentrated in vacuo to afford the title compound as a glassy material (2.9 g, 99%). 1H NMR (400 MHz, CDCl3) δ 4.91-4.53 (m, 1H), 3.06-2.47 (m, 2H), 1.61-1.04 (m, 11H), 0.27 (d, J=6.8 Hz, 6H); MS(ESI+) m/z 260.1 (M+H)+.

Workup

  1. customThe resulting reaction mixture
  2. extractionThe resulting aqueous layer was extracted with ethyl ether (2×)
  3. dry with materialThe organic solution was dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7493d88bd46d4591862370db5d605469
Source dataset
uspto-grants-2016_05
Patent number
US09345740B2

Reaction notes

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