Acetone → tert-butyl (3RS,4RS)-3-hydroxy-4-(4-prop-2-ynyloxy-phenyl)-piperidine-1-carboxylate

HRID 111241Notes

Reaction equation

HRID 111241 reaction equation
[C:26](=[O:27])([O-:28])[O-:29].[CH2:22]([C:23]#[CH:24])[Br:25].[CH3:32][C:33](=[O:34])[CH3:35].[K+:30].[K+:31].[OH:1][CH:2]1[CH2:3][N:4]([C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:5][CH2:6][CH:7]1[c:8]1[cH:9][cH:10][c:11]([OH:14])[cH:12][cH:13]1>>[OH:1][CH:2]1[CH2:3][N:4]([C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:5][CH2:6][CH:7]1[c:8]1[cH:9][cH:10][c:11]([O:14][CH2:24][C:23]#[CH:22])[cH:12][cH:13]1

Participants

6

Reactant 5

HCID 180AcetoneHCID 813Potassium Cation2×HCID 7842Propargyl bromideHCID 19660Carbonate IonHCID 21713087(3S,4S)-tert-Butyl 3-hydroxy-4-(4-hydroxyphenyl)piperidine-1-carboxylate

Product 1

HCID 54010348tert-butyl (3RS,4RS)-3-hydroxy-4-(4-prop-2-ynyloxy-phenyl)-piperidine-1-carboxylate

Sources & evidence

ORD record
ord-729506b0933940c5a77522086996be06
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (2/10)

Reaction notes

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