HCID 19914911, compound → HCID 19914940, compound

HRID 1650285Notes

Reaction equation

HRID 1650285 reaction equation
C([N:8]1[CH:12]([CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[CH2:11][CH2:10][CH:9]1[CH2:22][OH:23])C1C=CC=CC=1.[H][H]>CO.[OH-].[OH-].[Pd+2]>[Si:15]([O:14][CH2:13][CH:12]1[NH:8][CH:9]([CH2:22][OH:23])[CH2:10][CH2:11]1)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]

Participants

5

Reactant 2

HCID 19914911HCID 19914911, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19914940HCID 19914940, compoundYield 86.8%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-benzyl-5-t-butyldimethylsilyloxymethyl-2-hydroxymethylpyrrolidine (6.3 g) in methanol (63 ml) was added palladium hydroxide on carbon (630 mg) under nitrogen atmosphere. The apparatus was evacuated to remove nitrogen, then filled with hydrogen, and the mixture was stirred under hydrogen atmosphere until 19 mmol of hydrogen was absorbed. The palladium hydroxide on carbon was filtered off and the solvent was removed under reduced pressure to give 5-t-butyldimethylsilyloxymethyl-2-hydroxymethylpyrrolidine (4.0 g). To a solution of this residue in tetrahydrofuran (60 ml) and water (30 ml) were added sodium bicarbonate (4.10 g) and then allyl chloroformate (1.42 ml) at room temperature. After stirring for 2 hours, sodium bicarbonate (2.1 g) and allyloxycarbonyl chloride (1.42 ml) was added. After stirring for an hour, ethyl acetate (100 ml) and water (50 ml) were added and the aqueous layer was separated and extracted twice with ethyl acetate. The combined organic layer was washed with 1N hydrochloric acid, saturated aqueous sodium bicarbonate, water and brine successively, dried over magnesium sulfate and evaporated under reduced pressure. The residue was column chromatographed on silica gel (eluent:hexane/ethyl acetate, 9:1-4:1 V/V) to give 1-allyloxycarbonyl-5-t- butyldimethylsilyloxymethyl-2-hydroxymethylpyrrolidine (4.91 g).

Workup

  1. customThe apparatus was evacuated
  2. customto remove nitrogen
  3. additionfilled with hydrogen
  4. customwas absorbed
  5. filtrationThe palladium hydroxide on carbon was filtered off
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-6e826815e0bc42559696616a62f56cdc
Source dataset
uspto-grants-1990_05
Patent number
US04923857

Reaction notes

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