Triphenylphosphine → (S)-3-(5-Bromopyridin-3-yloxy)-piperidine-1-carboxylic acid tert-butyl ester

HRID 1774759Notes

Reaction equation

HRID 1774759 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][CH2:19][C@@H:18](O)[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][CH2:19][C@H:18]([O:8][C:4]2[CH:5]=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=2)[CH2:17]1)=[O:15])([CH3:12])([CH3:10])[CH3:11]

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 5995293-Bromo-5-hydroxypyridineHCID 1514398(R)-1-Boc-3-hydroxypiperidineHCID 16218364(4-chlorophenyl)methyl (NZ)-N-[(4-chlorophenyl)methoxycarbonylimino]carbamate

Product 1

HCID 86679136(S)-3-(5-Bromopyridin-3-yloxy)-piperidine-1-carboxylic acid tert-butyl ester

Procedure

In analogy to the procedure described for the preparation of intermediate A-7, 5-bromopyridin-3-ol was reacted with (R)-3-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 oil. MS: 357.1 and 359.1 (M+H+).

Sources & evidence

ORD record
ord-ec2ee13cc733427085b2232b053cc23c
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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