Lithium iodide → HCID 53779416, compound

HRID 975636Notes

Reaction equation

HRID 975636 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[CH2:9][C@H:8]1[CH:20]=[CH:21][C:22](OC)=[O:23])=[O:6])[CH:2]=[CH2:3].[BH4-].[Na+].[I-].[Li+]>O1CCCC1.O>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][Si:13]([C:16]([CH3:17])([CH3:18])[CH3:19])([CH3:15])[CH3:14])[CH2:9][C@H:8]1[CH2:20][CH2:21][CH2:22][OH:23])=[O:6])[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 66321Lithium iodideHCID 4311764Sodium borohydrideHCID 54265678HCID 54265678, compound

Product 1

HCID 53779416HCID 53779416, compoundYield 98.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2S,4R)-1-allyloxycarbonyl-4-t-butyldimethylsilyloxy-2-(3-methoxy-3-oxo-1-propenyl)pyrrolidine (18.7 g) in tetrahydrofuran (190 ml) were added successively sodium borohydride (3.83 g) and lithium iodide (13.5 g) at room temperature and the mixture was refluxed for 4 hours. After cooling to room temperature, the mixture was diluted with water (200 ml) and extracted with ethyl acetate (200 ml×3). The combined extracts were washed with brine (400 ml), dried over magnesium sulfate and concentrated to give (2R,4R)-1-allyloxycarbonyl-4-t-butyldimethylsilyloxy-2-(3-hydroxypropyl)pyrrolidine (17.2 g) as a pale yellow paste.

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. extractionextracted with ethyl acetate (200 ml×3)
  3. washThe combined extracts were washed with brine (400 ml)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-421a8430511f4304937ecaa5ed70c91d
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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