(S)-tert-Butyl 3-(bromomethyl)piperidine-1-carboxylate → 1,1-Dimethylethyl (3R)-3-{[6-amino-2-(butyloxy)-8-(methyloxy)-9H-purin-9-yl]methyl}-1-piperidinecarboxylate

HRID 1044853Notes

Reaction equation

HRID 1044853 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][CH3:15])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([O:30][CH3:31])[N:6]2[CH2:16][CH:17]1[CH2:22]CN(C(OC(C)(C)C)=O)[CH2:19][CH2:18]1.FC(F)(F)C(O)=O.C(OC1N=C2C(N=C(OC)N2)=C(N)N=1)CCC.BrC[C@H]1CCC[N:60]([C:64]([O:66][C:67]([CH3:70])([CH3:69])[CH3:68])=[O:65])[CH2:59]1>>[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][CH3:15])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([O:30][CH3:31])[N:6]2[CH2:16][C@H:17]1[CH2:18][CH2:19][CH2:59][N:60]([C:64]([O:66][C:67]([CH3:70])([CH3:69])[CH3:68])=[O:65])[CH2:22]1

Participants

4

Reactant 3

HCID 34177035(S)-tert-Butyl 3-(bromomethyl)piperidine-1-carboxylateHCID 583060912-Butoxy-9-(1-tert-butoxycarbonylpiperidin-4-ylmethyl)-8-methoxyadenineHCID 178450370HCID 178450370, compound

Product 1

HCID 672335791,1-Dimethylethyl (3R)-3-{[6-amino-2-(butyloxy)-8-(methyloxy)-9H-purin-9-yl]methyl}-1-piperidinecarboxylate

Procedure

Prepared similarly to Intermediate 13 from 2-butoxy-8-methoxy-9H-purin-6-amine trifluoroacetate salt and 1,1-dimethylethyl (3S)-3-(bromomethyl)-1-piperidinecarboxylate.

Sources & evidence

ORD record
ord-32b25e78fb884c30a7f4c137c4d3df00
Source dataset
uspto-grants-2013_10
Patent number
US08563717B2

Reaction notes

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