tert-Butyl (1R,4R)-4-(3-nitrobenzylamino)cyclohexylcarbamate → HCID 62314401, compound

HRID 1054026Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([CH:23]=[CH:24][CH:25]=1)[CH2:7][NH:8][CH:9]1[CH2:14][CH2:13][CH:12]([NH:15]C(=O)OC(C)(C)C)[CH2:11][CH2:10]1)([O-:3])=[O:2]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[N+:1]([C:4]1[CH:5]=[C:6]([CH:23]=[CH:24][CH:25]=1)[CH2:7][NH:8][CH:9]1[CH2:10][CH2:11][CH:12]([NH2:15])[CH2:13][CH2:14]1)([O-:3])=[O:2]

Participants

Conditions

Temperature: 30 °C

Procedure

Tert-butyl N-(4-[(3-nitrobenzyl)amino]cyclohexyl)carbamate (30.0 g, 86.1 mmol, 1.0 eq) was dissolved in 300 mL of TFA:DCM (1:10) and the resulting solution was stirred at 30° C. overnight. The reaction mixture was then concentrated under vacuum to provide crude 1-N-(3-nitrobenzyl)cyclohexane-1,4-diamine (32 g, TFA salt) as a white solid.

Workup

concentrationThe reaction mixture was then concentrated under vacuum

Sources & evidence

ORD record: ord-f4bc9f8d7c2c45d8bf798e92efc446da
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394286B2

Reaction notes

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