Triphenylphosphine → 3-bromo-5-[[1-(tert-butoxycarbonyl)-2(R)-pyrrolidinyl]methoxy]pyridine

HRID 1774778Notes

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[CH2:20][CH2:19][CH2:18][C@@H:17]1[CH2:21]O)=[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[CH2:20][CH2:19][CH2:18][C@@H:17]1[CH2:21][O:8][C:4]1[CH:5]=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=1)=[O:15])([CH3:12])([CH3:10])[CH3:11]

Participants

Reactant 4

HCID 11776Triphenylphosphine

HCID 5995293-Bromo-5-hydroxypyridine

HCID 688279N-(tert-Butoxycarbonyl)-D-prolinol

HCID 16218364(4-chlorophenyl)methyl (NZ)-N-[(4-chlorophenyl)methoxycarbonylimino]carbamate

Product 1

HCID 154802363-bromo-5-[[1-(tert-butoxycarbonyl)-2(R)-pyrrolidinyl]methoxy]pyridine

Procedure

In analogy to the procedure described for the preparation of intermediate A-7, 5-bromopyridin-3-ol was reacted with (R)-2-(hydroxymethyl)pyrrolidine-1-carboxylic acid tert-butyl ester in presence of di-(4-chlorobenzyl)azodicarboxylate and triphenylphosphine to give the title compound as an orange oil. MS: 357.3 and 359.3 (M+H+).

Sources & evidence

ORD record: ord-8bc681f819af4e509adc5af97b178bc6
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260408B2

Reaction notes

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