Tetrabutylammonium Fluoride → 1-Benzyloxycarbonyl-3-(S)-hydroxy-4-(R)-(1-ethoxycarbonylcyclopropyl)pyrrolidine

HRID 635074Notes

Reaction equation

HRID 635074 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@@H:14]([C:16]2([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:18][CH2:17]2)[C@H:13]([O:24][Si](C(C)(C)C)(C)C)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@@H:14]([C:16]2([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:17][CH2:18]2)[C@H:13]([OH:24])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 219712601-Benzyloxycarbonyl-3-(S)-tert-butyldimethylsilyloxy-4-(R)-(1-ethoxycarbonylcyclopropyl)pyrrolidine

Product 1

HCID 219712591-Benzyloxycarbonyl-3-(S)-hydroxy-4-(R)-(1-ethoxycarbonylcyclopropyl)pyrrolidineYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1-Benzyloxycarbonyl-3-(S)-tert-butyldimethylsilyloxy-4-(R)-(1-ethoxycarbonylcyclopropyl)pyrrolidine (1.79 g, 4.00 mmol) was dissolved in tetrahydrofuran (40 ml) to which, cooled in an ice bath, was subsequently added dropwise a tetrahydrofuran solution of 1.0 M tetrabutylammonium fluoride (5.33 ml, 5.33 mmol). The reaction solution was stirred at room temperature for 30 minutes and then tetrahydrofuran was evaporated under reduced pressure. Thereafter, the resulting residue was subjected to flash silica gel chromatography and eluted with an eluant of n-hexane:ethyl acetate=1:1, to thereby obtain 1.04 g (76%) of the title compound as a colorless oil.

Workup

  1. temperaturecooled in an ice bath
  2. customtetrahydrofuran was evaporated under reduced pressure
  3. washeluted with an eluant of n-hexane

Sources & evidence

ORD record
ord-4941c2982eee405e859e533c3e282009
Source dataset
uspto-grants-2001_02
Patent number
US06184388B2

Reaction notes

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