Exo-8-boc-8-azabicyclo[3.2.1]octane-3-carboxylic acid methyl ester → 2'-tert-butyl-4',6'-dihydro-8-azaspiro[bicyclo[3.2.1]octane-3,5'-pyrazolo[3,4-c]pyridin]-7'(2'H)-one hydrochloride

HRID 880922Notes

Reaction equation

HRID 880922 reaction equation
[ClH:1].[CH:2]([N:5]1[CH:13]=[C:12]2[C:7]([C:8](=[O:19])[NH:9][C:10]3([CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[CH2:11]2)=[N:6]1)([CH3:4])[CH3:3].[C@@H:20]12N(C(OC(C)(C)C)=O)[C@@H](CC1)CC(C(OC)=O)[CH2:21]2.[C:39](N1C=C(CI)C(I)=N1)(C)(C)C>>[ClH:1].[C:2]([N:5]1[CH:13]=[C:12]2[C:7]([C:8](=[O:19])[NH:9][C:10]3([CH2:14][CH:15]4[NH:16][CH:17]([CH2:20][CH2:21]4)[CH2:18]3)[CH2:11]2)=[N:6]1)([CH3:39])([CH3:4])[CH3:3]

Participants

4

Reactant 3

HCID 67491395Exo-8-boc-8-azabicyclo[3.2.1]octane-3-carboxylic acid methyl esterHCID 674915642'-isopropyl-4',6'-dihydrospiro[piperidine-4,5'-pyrazolo[3,4-c]pyridin]-7'(2'H)-one hydrochlorideHCID 674917761-tert-butyl-3-iodo-4-(iodomethyl)-1H-pyrazole

Product 1

HCID 674914372'-tert-butyl-4',6'-dihydro-8-azaspiro[bicyclo[3.2.1]octane-3,5'-pyrazolo[3,4-c]pyridin]-7'(2'H)-one hydrochloride

Procedure

The title compound was prepared by a method analogous to that described for Intermediate 3, Steps 4-8, using (1R,5S)-8-tert-butyl 3-methyl 8-azabicyclo[3.2.1]octane-3,8-dicarboxylate and 1-tert-butyl-3-iodo-4-(iodomethyl)-1H-pyrazole. +ESI (M+H) 289.2; 1H NMR (400 MHz, CD3OD, δ): 7.69 (s, 1H), 4.03-4.10 (m, 2H), 2.74 (s, 2H), 2.39-2.46 (m, 2H), 2.10-2.25 (m, 6H), 1.59 (s, 9H).

Sources & evidence

ORD record
ord-2c30adcb9f5840b68fff8187bb72cca1
Source dataset
uspto-grants-2015_03
Patent number
US08993586B2

Reaction notes

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