Hydrochloric Acid → (2S,4R)-1-benzyloxycarbonyl-2-(4-hydroxy-2-butenyl)oxymethyl-4-methanesulfonyloxypyrrolidine

HRID 703586Notes

Reaction equation

HRID 703586 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([O:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH2:13][C@H:12]1[CH2:21][O:22][CH2:23][CH:24]=[CH:25][C:26](OCC)=[O:27])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.Cl>O1CCCC1.C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([O:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH2:13][C@H:12]1[CH2:21][O:22][CH2:23][CH:24]=[CH:25][CH2:26][OH:27])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 57248036(2S,4R)-1-benzyloxycarbonyl-2-[{3-(ethoxycarbonyl)-2-propenyl}oxymethyl]-4-methanesulfonyloxypyrrolidine

Product 1

HCID 57283785(2S,4R)-1-benzyloxycarbonyl-2-(4-hydroxy-2-butenyl)oxymethyl-4-methanesulfonyloxypyrrolidineYield 56%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (2S,4R)-1-benzyloxycarbonyl-2-[{3-(ethoxycarbonyl)-2-propenyl}oxymethyl]-4-methanesulfonyloxypyrrolidine (10 g) in tetrahydrofuran (120 ml) was added dropwise 1.0 M solution of diisobutylaluminum hydride in toluene (56.6 ml) at -40° C. and the mixture was allowed to warm to 0° C. and stirred for 10 hours at the same temperature. The reaction mixture was added dropwise 1N hydrochloric acid (50 ml), and the resulting precipitate was filtered off. The filtrate was dissolved in a mixture of ethyl acetate (200 ml) and water (100 ml). The organic layer was separated, washed with brine (100 ml), dried over magnesium sulfate and treated with active carbon. Evaporation of the solvent gave a residue, which was chromatographed on silica gel (200 ml) eluting with a mixture of hexane and ethyl acetate (1:4 V/V) to give (2S,4R)-1-benzyloxycarbonyl-2-(4-hydroxy-2-butenyl)oxymethyl-4-methanesulfonyloxypyrrolidine (5.07 g).

Workup

  1. filtrationthe resulting precipitate was filtered off
  2. dissolutionThe filtrate was dissolved in a mixture of ethyl acetate (200 ml) and water (100 ml)
  3. customThe organic layer was separated
  4. washwashed with brine (100 ml)
  5. dry with materialdried over magnesium sulfate
  6. additiontreated with active carbon
  7. customEvaporation of the solvent
  8. customgave a residue, which
  9. customwas chromatographed on silica gel (200 ml)
  10. washeluting with a mixture of hexane and ethyl acetate (1:4 V/V)

Sources & evidence

ORD record
ord-b0c5b48f25784d89b656d49867df56d0
Source dataset
uspto-grants-1991_01
Patent number
US04983596

Reaction notes

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