tert-Butyl piperazine-1-carboxylate → HCID 86694443, compound

HRID 1519509Notes

Reaction equation

HRID 1519509 reaction equation
O=[C:2]1[CH2:11][C:10]2[CH:9]=[C:8]([N:12]3[C:20](=[O:21])[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13]3=[O:22])[CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3]1.[C:23]([N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24].C([BH3-])#N.[Na+]>CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].C(O)C>[C:26]([O:25][C:23]([N:30]1[CH2:35][CH2:34][N:33]([CH:2]2[CH2:3][CH2:4][C:5]3[C:10](=[CH:9][C:8]([N:12]4[C:20](=[O:21])[C:19]5[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=5)[C:13]4=[O:22])=[CH:7][CH:6]=3)[CH2:11]2)[CH2:32][CH2:31]1)=[O:24])([CH3:29])([CH3:27])[CH3:28]

Participants

6

Reactant 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 5003444Sodium cyanoborohydrideHCID 67517443HCID 67517443, compound

Product 1

HCID 86694443HCID 86694443, compound

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 702EthanolSolvent

Procedure

To a flask charged with 2-(7-oxo-5,6,7,8-tetrahydronaphthalen-2-yl)-1H-isoindole-1,3(2H)-dione (0.25 g, 0.86 mmol), N-Boc piperazine (0.24 g, 1.3 mmol), and a stir bar was added titanium isopropoxide (2.5 mL), ethanol (10 mL), and sodium cyanoborohydride (0.27 g, 4.3 mmol). The mixture was allowed to stir at RT for 2 hours. LC showed formation of the desired product at that point. The reaction was diluted with EtOAc (50 mL), washed with water and brine, dried over sodium sulfate, filtered and concentrated, and purified by MPLC to afford the desired product. LC-MS (IE, m/z): 462 [M+1]+.

Sources & evidence

ORD record
ord-5c5b35c8ecfd4bdead5d823075d4c1a6
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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