Lithium hydroxide, monohydrate → HCID 58865564, compound

HRID 1354844Notes

Reaction equation

HRID 1354844 reaction equation
[C:1]([O:5][C:6](=[O:28])[NH:7][C@H:8]1[CH2:12][C@@H:11]([CH2:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[N:10](C(=O)C(F)(F)F)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].O[Li].O>O1CCOCC1>[C:1]([O:5][C:6](=[O:28])[NH:7][C@H:8]1[CH2:12][C@@H:11]([CH2:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[NH:10][CH2:9]1)([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 58949399HCID 58949399, compound

Product 1

HCID 58865564HCID 58865564, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 327 (16.0 mmol) in 1,4-dioxane (120 mL) was added LiOH.H2O (32.0 mmol, 2 equiv). The suspension was allowed to stir at room temperature for 16 h at which point TLC indicated complete consumption of starting material (KMnO4 stain for S.M.). The reaction was diluted with THF (120 mL), filtered through a glass frit and concentrated. The resulting syrup was diluted with THF/CHCl3 (1:1, 200 mL) and washed with saturated NaHCO3 (100 mL), brine (100 mL), dried (MgSO4), and purified via column chromatography (0–10% MeOH in CH2Cl2 with 0–1% NH4OH) to give [5-(S)-(tert-Butoxycarbonylamino-methyl)-pyrrolidin-3-(S)-yl]-carbamic acid tert-butyl ester (328) as a colorless foam. 1H NMR (400 MHz, CD3OD) δ=1.45 ppm (s, 9H), 1.47 (s, 9H), 1.69 (br s, 1H), 2.32–2.39 (m, 1H), 2.82 (dd, 1H, J=6, 13 Hz), 2.89 (dd, 1H, J=4, 13 Hz), 3.00 (dd, 1H, J=7, 11 Hz), 3.81 (dd, 1H, J=7, 11 Hz), 3.92–3.98 (m, 1H); 13C NMR (100 MHz, DMSO-d6) δ=26.0, 29.0, 29.1, 58.9, 67.8, 78.5, 79.1, 154.3, 155.7 pm.

Workup

  1. customconsumption of starting material (KMnO4 stain for S.M.)
  2. additionThe reaction was diluted with THF (120 mL)
  3. filtrationfiltered through a glass frit
  4. concentrationconcentrated
  5. additionThe resulting syrup was diluted with THF/CHCl3 (1:1, 200 mL)
  6. washwashed with saturated NaHCO3 (100 mL), brine (100 mL)
  7. dry with materialdried (MgSO4)
  8. custompurified via column chromatography (0–10% MeOH in CH2Cl2 with 0–1% NH4OH)

Sources & evidence

ORD record
ord-7b0023a08b884270a4eeddec4128285a
Source dataset
uspto-grants-2007_05
Patent number
US07223759B2

Reaction notes

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