Sodium borohydride → HCID 71060655, compound

HRID 1036721Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1([CH:19]([C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)[CH2:20][N+:21]([O-])=O)[CH2:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]1)=[O:5])[CH3:2].[BH4-].[Na+]>CO.O.O.O.O.O.O.[Ni](Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1([CH:19]([C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)[CH2:20][NH2:21])[CH2:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:16])[CH3:17])=[O:13])[CH2:7]1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 3-(2-Nitro-1-pyridin-3-yl-ethyl)piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (2.92 g, 7.17 mmol) in MeOH (60 ml) was added nickel chloride hexahydrate (1.70 g, 7.17 mmol) and the mixture was cooled in an ice bath. Sodium borohydride (1.08 g, 28.7 mmol) was portionwise added over 30 minutes and the resulting suspension was stirred for further 30 minutes at 0° C. The reaction was quenched with saturated NH4Cl solution (30 ml) and MeOH was removed in vacuo. The aqueous residue was extracted with EtOAc (2×50 ml) and DCM (2×50 ml). The combined organic extracts were dried (MgSO4) and concentrated in vacuo to afford the title compound which was used without further purification.

Workup

temperaturethe mixture was cooled in an ice bath
customThe reaction was quenched with saturated NH4Cl solution (30 ml) and MeOH
customwas removed in vacuo
extractionThe aqueous residue was extracted with EtOAc (2×50 ml) and DCM (2×50 ml)
dry with materialThe combined organic extracts were dried (MgSO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-90e0f6b24ce448d680f4bcfe663dea0d
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546416B2

Reaction notes

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