Sodium Thiosulfate → tert-Butyl 4-(2-oxoethyl)piperidine-1-carboxylate
Reaction equation
[OH:1][CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1.CC1(C)N([O])C(C)(C)CCC1.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[CH:2]([CH2:3][CH:4]1[CH2:5][CH2:6][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:8][CH2:9]1)=[O:1]Participants
Procedure
To a flask containing tert-butyl 4-(2 hydroxyethyl)piperidine-1-carboxylate (4.4 g, 19.2 mmol) in CH2Cl2 (20 mL) was added TEMPO (300 mg, 1.92 mmol) followed by iodobenzene diacetate (6.8 g, 21.1 mmol). The reaction was stirred 3 hours and then diluted with CH2Cl2 (100 mL). Saturated aqueous solution of Na2S2O3 (100 mL) was added and extracted with CH2Cl2 (3×50 mL). The combined organics were washed with saturated aqueous NaHCO3 (150 mL) and brine (150 mL), dried over Na2SO4, and concentrated in vacuo. The resulting residue was purified by silica gel chromatography (40-70% Et2O/pentanes) to provide the title compound, which was identical to the reported literature compound (see Sato et al. (2001) Heterocycle 54: 747). 13C NMR (75 MHz, CDCl3) δ 201.5, 154.7, 79.4, 50.3, 43.7, 31.9, 30.6, 28.4.
Workup
- extractionextracted with CH2Cl2 (3×50 mL)
- washThe combined organics were washed with saturated aqueous NaHCO3 (150 mL) and brine (150 mL)
- dry with materialdried over Na2SO4
- concentrationconcentrated in vacuo
- customThe resulting residue was purified by silica gel chromatography (40-70% Et2O/pentanes)
Sources & evidence
- ORD record
- ord-1d8544f64d794995bd473023db2d87b3
- Source dataset
- uspto-grants-2007_09
- Patent number
- US07265249B2
Reaction notes
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