1,2-Dichloroethane → tert-Butyl 3-(1-Pivaloyl-1H-indazol-5-ylamino)piperidine-1-carboxylate

HRID 1911991Notes

Reaction equation

O=[C:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.ClCCCl.C(O)(=O)/C=C\C(O)=O.[NH2:27][C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][CH:36]=1)[N:33]([C:37](=[O:42])[C:38]([CH3:41])([CH3:40])[CH3:39])[N:32]=[CH:31]2.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(=O)(O)[O-].[Na+]>[C:37]([N:33]1[C:34]2[C:30](=[CH:29][C:28]([NH:27][CH:2]3[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]3)=[CH:36][CH:35]=2)[CH:31]=[N:32]1)(=[O:42])[C:38]([CH3:41])([CH3:40])[CH3:39]

Participants

Conditions

Temperature: 20 °C

Procedure

Into a 1 L 3-neck round bottom flask fitted with a nitrogen inlet and mechanical stirrer was added tert-butyl 3-oxopiperidine-1-carboxylate (14.2 g, 0.07 mol), 1,2-dichloroethane (300 mL), and 1-(5-amino-1H-indazol-1-yl)-2,2-dimethylpropan-1-one maleate salt (23.0 g, 0.07 mol). The vessel was purged with nitrogen and stirred at 20° C. for one hour. Sodium triacetoxyborohydride (19.0 g, 0.09 mol) was added, and the reaction was monitored by analytical TLC to completion. The reaction was diluted with 100 mL of saturated sodium bicarbonate. The organic phase was isolated, dried over MgSO4, filtered and evaporated to dryness to afford the title compound as a yellow solid (25.0 g, 91%).

Workup

customInto a 1 L 3-neck round bottom flask fitted with a nitrogen inlet and mechanical stirrer
customThe vessel was purged with nitrogen
customThe organic phase was isolated
dry with materialdried over MgSO4
filtrationfiltered
customevaporated to dryness

Sources & evidence

ORD record: ord-9fbb86af749941089a178d466d775f55
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08604218B2

Reaction notes

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