Triphenylphosphine → tert-Butyl 4-((5-bromopyridin-3-yl)oxy)piperidine-1-carboxylate

HRID 1774760Notes

Reaction equation

HRID 1774760 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[N:6][CH:7]=1.[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][CH:19](O)[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].C1C(COC(/N=N\C(OCC2C=CC(Cl)=CC=2)=O)=O)=CC=C(Cl)C=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>>[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][CH:19]([O:8][C:4]2[CH:5]=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=2)[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:10])[CH3:11]

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 5995293-Bromo-5-hydroxypyridineHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 16218364(4-chlorophenyl)methyl (NZ)-N-[(4-chlorophenyl)methoxycarbonylimino]carbamate

Product 1

HCID 68979532tert-Butyl 4-((5-bromopyridin-3-yl)oxy)piperidine-1-carboxylate

Procedure

In analogy to the procedure described for the preparation of intermediate A-7, 5-bromopyridin-3-ol was reacted with 4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester in presence of di-(4-chlorobenzyl)azodicarboxylate and triphenylphosphine to give the title compound as a light yellow amorphous solid. MS: 357.0 and 359.0 (M+H+).

Sources & evidence

ORD record
ord-e991232ce24c4b448b11c60229f50a68
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

Loading…