Lithium iodide → HCID 15671481, compound

HRID 1088272Notes

Reaction equation

HRID 1088272 reaction equation
C[O:2][C:3](=O)[C@@H:4]1[CH2:8][C@@H:7]([O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])[CH2:6][N:5]1[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)=[O:18].[BH4-].[Na+].[I-].[Li+]>O1CCCC1.O>[CH3:28][O:27][C:24]1[CH:23]=[CH:22][C:21]([CH2:20][O:19][C:17]([N:5]2[CH2:6][C@H:7]([O:9][Si:10]([C:13]([CH3:16])([CH3:14])[CH3:15])([CH3:12])[CH3:11])[CH2:8][C@H:4]2[CH2:3][OH:2])=[O:18])=[CH:26][CH:25]=1

Participants

6

Reactant 3

HCID 66321Lithium iodideHCID 4311764Sodium borohydrideHCID 15671478HCID 15671478, compound

Product 1

HCID 15671481HCID 15671481, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

trans-1-(p-Methoxybenzyloxycarbonyl)-4-t-butyldimethylsilyloxy-L-proline methyl ester (5.64 g) was dissolved in 56.4 ml of dry tetrahydrofuran. Sodium borohydride (1.01 g) and lithium iodide (3.52 g) were added thereto. The resulting mixture was refluxed for 1 hour, diluted with water, extracted with ethyl acetate, washed with water, dried over anhydrous sodium sulfate and distilled off to obtain (2S,4R)-1-(p-methoxybenzyloxycarbonyl)-2-hydroxymethyl-4-t-butyldimethylsilyloxypyrrolidine.

Workup

  1. temperatureThe resulting mixture was refluxed for 1 hour
  2. extractionextracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationdistilled off

Sources & evidence

ORD record
ord-904c704390434070aee09ded6e75566f
Source dataset
uspto-grants-1990_10
Patent number
US04962103

Reaction notes

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