HCID 97107398, compound → tert-Butyl (3S,4S)-3-hydroxy-4-(4-hydroxyphenyl)piperidine-1-carboxylate

HRID 716077Notes

Reaction equation

HRID 716077 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][C@H:16]2[OH:28])=[CH:11][CH:10]=1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[OH:28][C@H:16]1[C@H:15]([C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=2)[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17]1

Participants

5

Reactant 2

HCID 97107398HCID 97107398, compound2×HCID 178418361HCID 178418361, compound

Product 1

HCID 24820608tert-Butyl (3S,4S)-3-hydroxy-4-(4-hydroxyphenyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (3S,4S)-tert-butyl 4-(4-(benzyloxy)phenyl)-3-hydroxypiperidine-1-carboxylate (26 g, 67.8 mmol, intermediate C) in 260 mL of methanol was treated with 1.6 grams of 10% palladium on carbon (13.6 mmol) in a pressure bottle. Hydrogen at 50 psi was introduced, and the reaction mixture was stirred for 16 h.

Sources & evidence

ORD record
ord-584a45e977b947cc8ba937722bee2f04
Source dataset
uspto-grants-2015_11
Patent number
US09187506B2

Reaction notes

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