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Methyl iodide → tert-butyl (2R,4R) 4-(tert-butyl-dimethyl-silyl)oxy-2-(methoxymethyl)pyrrolidine-1-carboxylate

HRID 908450
Notes
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Reaction equation

HRID 908450 reaction equation
[C:1]([Si:5]([CH3:22])([CH3:21])[O:6][C@H:7]1[CH2:11][N:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C@@H:9]([CH2:19][OH:20])[CH2:8]1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH3:26]>CN(C=O)C>[C:1]([Si:5]([CH3:22])([CH3:21])[O:6][C@H:7]1[CH2:11][N:10]([C:12]([O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:13])[C@@H:9]([CH2:19][O:20][CH3:26])[CH2:8]1)([CH3:4])([CH3:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 14117005(2R,4R)-tert-Butyl 4-((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

Product 1

HCID 67388742tert-butyl (2R,4R) 4-(tert-butyl-dimethyl-silyl)oxy-2-(methoxymethyl)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent
2×

Conditions

Temperature
20 °C

Procedure

A solution of tert-butyl (2R,4R) 4-(tert-butyl-dimethyl-silyl)oxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate (9.32 g) in DMF (15 ml) was added to a stirred suspension of sodium hydride (60% dispersion) (1.37 g) in DMF 100 ml) at −10° C. Iodomethane (2.13 ml) was added and the reaction allowed to warm to 20° C. The reaction mixture was quenched carefully with water and evaporated to dryness. The crude material was partitioned between ethyl acetate (250 ml) and water (100 ml). The organic layer was washed with brine (100 ml), dried over Magnesium sulphate, filtered and evaporated to give tert-butyl (2R,4R) 4-(tert-butyl-dimethyl-silyl)oxy-2-(methoxymethyl)pyrrolidine-1-carboxylate (6.68 g) as a colourless oil. NMR Spectrum: (DMSOd6) 0.02 (6H, s); 0.83-0.84 (9H, s); 1.36 (9H, s); 1.78 (1H, d); 1.99 (1H, s); 2.99 (1H, d); 3.19 (3H, d); 3.23-3.48 (3H, m); 3.80 (1H, s); 4.33 (1H, s).

Workup

  1. customThe reaction mixture was quenched carefully with water
  2. customevaporated to dryness
  3. customThe crude material was partitioned between ethyl acetate (250 ml) and water (100 ml)
  4. washThe organic layer was washed with brine (100 ml)
  5. dry with materialdried over Magnesium sulphate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-926cfebca1c54243a01a8b13c6509e5f
Source dataset
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08017611B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes