Imidazole → (S)-tert-Butyl 4-((R)-2-(((tert-butyldimethylsilyl)oxy)methyl)pent-4-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate

HRID 451845Notes

Reaction equation

HRID 451845 reaction equation
[OH:1][CH2:2][C@H:3]([CH2:19][CH:20]=[CH2:21])[CH2:4][C@H:5]1[CH2:9][O:8][C:7]([CH3:11])([CH3:10])[N:6]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].N1C=CN=C1.[CH3:27][C:28]([Si:31](Cl)([CH3:33])[CH3:32])([CH3:30])[CH3:29]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Si:31]([O:1][CH2:2][C@H:3]([CH2:19][CH:20]=[CH2:21])[CH2:4][C@H:5]1[CH2:9][O:8][C:7]([CH3:11])([CH3:10])[N:6]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])([C:28]([CH3:30])([CH3:29])[CH3:27])([CH3:33])[CH3:32]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 58011478(S)-tert-Butyl 4-((R)-2-(hydroxymethyl)pent-4-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate

Product 1

HCID 58011479(S)-tert-Butyl 4-((R)-2-(((tert-butyldimethylsilyl)oxy)methyl)pent-4-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylateYield 57%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (S)-tert-butyl 4-((R)-2-(hydroxymethyl)pent-4-enyl)-2,2-dimethyloxazolidine-3-carboxylate (11.5 g, 38.4 mmol), imidazole (7.84 g, 115.2 mmol) and DMAP (234 mg, 1.92 mmol) in CH2Cl2 (200 mL) was added a solution of TBSCl (8.68 g, 57.6 mmol) in CH2Cl2 (100 mL) dropwise. The reaction mixture was stirred at rt for overnight. The reaction was washed with water (100 mL) and the aqueous layer was extracted with CH2Cl2 (3×100 mL), the combined organic layers was washed with brine (70 mL), then dried over Na2SO4, filtered and concentrated to give the crude product, which was purified by column chromatography to afford (s)-tert-butyl 4-((R)-2-((tert-butyldimethylsilyloxy)methyl)pent-4-enyl)-2,2-dimethyloxazolidine-3-carboxylate (9 g, 57%).

Workup

  1. washThe reaction was washed with water (100 mL)
  2. extractionthe aqueous layer was extracted with CH2Cl2 (3×100 mL)
  3. washthe combined organic layers was washed with brine (70 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the crude product, which
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-fadde4678f7d4273a0dbc77b03611ec5
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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