Water → HCID 57970216, compound

HRID 1666671Notes

Reaction equation

HRID 1666671 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[C@@H:16]([O:17][Si](C(C)(C)C)(C)C)[CH2:15][N:14]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[C@@H:16]([OH:17])[CH2:15][N:14]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:13]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 67443009HCID 67443009, compound

Product 1

HCID 57970216HCID 57970216, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

t-Butyl (3R,4S)-3-benzyloxycarbonylamino-4-(t-butyldimethylsilanoxy)pyrrolidine-1-carboxylate (54 g) was dissolved in THF (400 mL), followed by addition of a solution (167 mL) of 1 M tetrabutyl ammonium fluoride in THF with ice cooling, and the mixture was stirred at room temperature for 3.5 h. Water was added, then the mixture was extracted with ethyl acetate, and the organic layer was dried with anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, hexane/ethyl acetate=1:1-1:2) to obtain t-butyl (3R,4S)-3-benzyloxycarbonylamino-4-hydroxypyrrolidine-1-carboxylate (38 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialthe organic layer was dried with anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography (silica gel, hexane/ethyl acetate=1:1-1:2)

Sources & evidence

ORD record
ord-99d2e3ff3ff24b62974ec5b82369a79e
Source dataset
uspto-grants-2011_10
Patent number
US08044068B2

Reaction notes

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