Water → (3R,4R)-4-(3-Bromo-phenyl)-3-hydroxy-piperidine-1-carboxylic acid t-butyl ester

HRID 1809796Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Br:20])[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC#N.[OH2:24]>>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C@H:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Br:20])[CH:15]=2)[C@@H:12]([OH:24])[CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 3

HCID 962Water

HCID 6342Acetonitrile

HCID 66836951tert-butyl 4-(3-bromophenyl)-3,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 67542384(3R*,4R*)-4-(3-Bromo-phenyl)-3-hydroxy-piperidine-1-carboxylic acid t-butyl ester

Procedure

The title compound is prepared analogously as described for the title B compound in Example 1 from the title A compound, 4-(3-bromo-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid t-butyl ester: MS 356.2/358.1 [M+H]+; retention time 6.59 min (HPLC, Nucleosil C18; 5→100% CH3CN in H2O within 8 min).

Sources & evidence

ORD record: ord-fbb98a918eff48f8a83bf622867ba45e
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362040B2

Reaction notes

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