Acetate → tert-butyl (3RS,4RS)-3-(1,4-dimethoxy-naphthalen-2-ylmethoxy)-4-(4-hydroxy-phenyl)-piperidine-1-carboxylate

HRID 1233156Notes

Reaction equation

HRID 1233156 reaction equation
[C:52]([O-:53])(=[O:54])[CH3:55].[C:56]([O-:57])(=[O:58])[CH3:59].[CH2:1]([CH:2]=[CH2:3])[O:4][c:5]1[cH:6][cH:7][c:8]([CH:11]2[CH:12]([O:24][CH2:25][c:26]3[c:27]([O:38][CH3:39])[c:28]4[cH:29][cH:30][cH:31][cH:32][c:33]4[c:34]([O:36][CH3:37])[cH:35]3)[CH2:13][N:14]([C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[CH2:15][CH2:16]2)[cH:9][cH:10]1.[CH3:49][CH2:50][OH:51].[ClH:48].[N:40]12[CH2:41][CH2:42][N:43]([CH2:44][CH2:45]1)[CH2:46][CH2:47]2.[Pd+2:60].[c:61]1([P:62]([c:63]2[cH:64][cH:65][cH:66][cH:67][cH:68]2)[c:69]2[cH:70][cH:71][cH:72][cH:73][cH:74]2)[cH:75][cH:76][cH:77][cH:78][cH:79]1.[c:80]1([P:81]([c:82]2[cH:83][cH:84][cH:85][cH:86][cH:87]2)[c:88]2[cH:89][cH:90][cH:91][cH:92][cH:93]2)[cH:94][cH:95][cH:96][cH:97][cH:98]1>>[OH:4][c:5]1[cH:6][cH:7][c:8]([CH:11]2[CH:12]([O:24][CH2:25][c:26]3[c:27]([O:38][CH3:39])[c:28]4[cH:29][cH:30][cH:31][cH:32][c:33]4[c:34]([O:36][CH3:37])[cH:35]3)[CH2:13][N:14]([C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[CH2:15][CH2:16]2)[cH:9][cH:10]1

Participants

8

Reactant 7

HCID 175Acetate2×HCID 313Hydrochloric AcidHCID 702EthanolHCID 9237DabcoHCID 11776Triphenylphosphine2×HCID 105144Allyl(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)chloropalladium(II)HCID 53648544tert-butyl (3RS,4RS)-4-(4-allyloxy-phenyl)-3-(1,4-dimethoxy-naphthalen-2-ylmethoxy)-piperidine-1-carboxylate

Product 1

HCID 54373685tert-butyl (3RS,4RS)-3-(1,4-dimethoxy-naphthalen-2-ylmethoxy)-4-(4-hydroxy-phenyl)-piperidine-1-carboxylate

Sources & evidence

ORD record
ord-c7ca6f796a38400caead9f693a1470ee
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (5/10)

Reaction notes

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