Dimethylformamide → 3,5-Dimethylbenzyl 4-((tert-butoxycarbonyl)amino)piperidine-1-carboxylate

HRID 1480461Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([CH2:9][OH:10])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[NH:11]1[CH2:16][CH2:15][CH:14]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:13][CH2:12]1.CN([CH:28]=[O:29])C>CCOC(C)=O>[C:20]([O:19][C:18]([NH:17][CH:14]1[CH2:13][CH2:12][N:11]([C:28]([O:10][CH2:9][C:4]2[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([CH3:1])[CH:3]=2)=[O:29])[CH2:16][CH2:15]1)=[O:24])([CH3:21])([CH3:23])[CH3:22]

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of (3,5-dimethylphenyl)methanol (1.020 g, 7.49 mmol) in DMF (5 mL) at RT was added CU (1.214 g, 7.49 mmol). The reaction mixture was heated at 50° C. for 20 hrs. Tert-butyl piperidin-4-ylcarbamate (1.5 g, 7.49 mmol) was added and the reaction mixture stirred at 50° C. for 4 hrs. The mixture was diluted with EtOAc and washed with a saturated solution of sodium bicarbonate, brine, dried over MgSO4, filtered and concentrated under reduced pressure. Purification was carried out by chromatography on silica using 0-100% EtOAc in hexanes as eluent to afford the title product.

Workup

washwashed with a saturated solution of sodium bicarbonate, brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customPurification

Sources & evidence

ORD record: ord-bc24c46074d4418d901dd95e79fde10b
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409895B2

Reaction notes

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