Methyl iodide → (S)-tert-butyl 4-(2-(1-methoxycyclopentyl)ethyl)-2,2-dimethyloxazolidine-3-carboxylate

HRID 451858Notes

Reaction equation

HRID 451858 reaction equation
[OH:1][C:2]1([CH2:7][CH2:8][C@H:9]2[CH2:13][O:12][C:11]([CH3:15])([CH3:14])[N:10]2[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:6][CH2:5][CH2:4][CH2:3]1.[H-].[Na+].[CH3:25]I>>[CH3:25][O:1][C:2]1([CH2:7][CH2:8][C@H:9]2[CH2:13][O:12][C:11]([CH3:15])([CH3:14])[N:10]2[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 68713316(S)-tert-butyl 4-(2-(1-hydroxycyclopentyl)ethyl)-2,2-dimethyloxazolidine-3-carboxylate

Product 1

HCID 59201438(S)-tert-butyl 4-(2-(1-methoxycyclopentyl)ethyl)-2,2-dimethyloxazolidine-3-carboxylateYield 95%

Procedure

The (S)-tert-butyl 4-(2-(1-hydroxycyclopentyl)ethyl)-2,2-dimethyloxazolidine-3-carboxylate was added to a suspension of NaH (568 mg, 14.2 mmol, 4.0 equiv) and the mixture stirred for 0.5 h. Methyl iodide (2.106 g, 14.2 mmol, 4.0 equiv) was added and the mixture stirred for 48 h at ambient temperature. The excess NaH was quenched by careful addition of water. The mixture was evaporated, and then taken up in EtOAc. The solution was washed with water, then brine and evaporated. The ether was purified by flash chromatography on silica, eluting with 0-41% EtOAc in hexanes. This afforded 1170 mg (3.4 mmol, 95% yield for two steps) of the desired (S)-tert-butyl 4-(2-(1-methoxycyclopentyl)ethyl)-2,2-dimethyloxazolidine-3-carboxylate.

Workup

  1. stirringthe mixture stirred for 48 h at ambient temperature
  2. customThe excess NaH was quenched by careful addition of water
  3. customThe mixture was evaporated
  4. washThe solution was washed with water
  5. custombrine and evaporated
  6. customThe ether was purified by flash chromatography on silica
  7. washeluting with 0-41% EtOAc in hexanes

Sources & evidence

ORD record
ord-fd6a8f5e778a4c7882f3636cdcb5996c
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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