3-Hydroxypyridine → HCID 16102636, compound
Reaction equation
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[OH:15][C@H:16]1[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17]1.[N:28]1[CH:33]=[CH:32][CH:31]=[C:30](O)[CH:29]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[N:28]1[CH:33]=[CH:32][CH:31]=[C:30]([O:15][C@@H:16]2[CH2:20][CH2:19][NH:18][CH2:17]2)[CH:29]=1Participants
Procedure
DIAD (0.631 mL, 3.20 mmol) in DCM (5 ml) was added dropwise to a mixture of (S)-tert-butyl 3-hydroxypyrrolidine-1-carboxylate (500 mg, 2.67 mmol), pyridin-3-ol (305 mg, 3.20 mmol) and triphenylphosphine (840 mg, 3.20 mmol) in DCM (20 ml), cooled in an ice bath. The mixture was allowed to warm to room temperature, stirred for 1 hour and then concentrated. The residue was dissolved in dioxan (15 mL) and 4M HCl in dioxan (15 mL) was added. The mixture was stirred for 1 hour and concentrated. The crude product was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M ammonia in methanol and pure fractions were evaporated to dryness to afford (3R)-3-(pyridin-3-yloxy)pyrrolidine (405 mg, 92%) as a colourless oil.
Workup
- temperaturecooled in an ice bath
- concentrationconcentrated
- dissolutionThe residue was dissolved in dioxan (15 mL)
- addition4M HCl in dioxan (15 mL) was added
- stirringThe mixture was stirred for 1 hour
- concentrationconcentrated
- customThe crude product was purified by ion exchange chromatography
- washThe desired product was eluted from the column
- customwere evaporated to dryness
Sources & evidence
- ORD record
- ord-74bf307a823647a18cddfe0c07e1ec79
- Source dataset
- uspto-grants-2011_08
- Patent number
- US08003649B2
Reaction notes
Loading…