Benzene, 1-ethoxy-2-iodo- → tert-butyl (R)-3-(2-ethoxyphenoxy)piperidine-1-carboxylate

HRID 2004418Notes

Reaction equation

HRID 2004418 reaction equation

[CH3:1][C:2]([O:5][C:6]([N:8]1[CH2:14][C@H:12]([OH:13])[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])[CH3:3].[CH3:15][CH2:16][O:17][c:18]1[c:23](I)[cH:22][cH:21][cH:20][cH:19]1>>[CH3:15][CH2:16][O:17][c:18]1[c:23]([O:13][C@H:12]2[CH2:14][N:8]([C:6]([O:5][C:2]([CH3:4])([CH3:3])[CH3:1])=[O:7])[CH2:9][CH2:10][CH2:11]2)[cH:22][cH:21][cH:20][cH:19]1

Participants

8

Reactant 2

HCID 136415Benzene, 1-ethoxy-2-iodo-

HCID 1514398(R)-1-Boc-3-hydroxypiperidine

Product 1

HCID 131737068tert-butyl (R)-3-(2-ethoxyphenoxy)piperidine-1-carboxylate

Reagents, catalysts & solvents 5

HCID 23683543Potassium t-amylateReagent

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

HCID 66978N,N'-Dimethyl-1,3-propanediamineCatalyst

HCID 312751,4-DioxaneSolvent

HCID 117669-PhenylanthraceneInternal standard

Conditions

Temperature: 100 °C

Sources & evidence

ORD record: ord-8b71e876631d45608c2dcd9446f688e5
Source dataset: 39k HTE dataset from Pfizer
DOI: 10.1038/s41557
Original link: View source

Reaction notes

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