4-Aminomethyl-1-N-Cbz-piperidine → HCID 68957831, compound

HRID 1784928Notes

Reaction equation

HRID 1784928 reaction equation
[O:1]1[CH2:3][CH:2]1[CH:4]([N:12]=[CH:13][B:14]=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[NH2:16][CH2:17][CH:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[CH2:20][CH2:19]1>C(O)(C)C>[OH:1][CH:2]([CH:4]([N:12]=[CH:13][B:14]=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:3][NH:16][CH2:17][CH:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][CH2:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)=[O:25])[CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 219554994-Aminomethyl-1-N-Cbz-piperidineHCID 86612600HCID 86612600, compound

Product 1

HCID 68957831HCID 68957831, compoundYield 121.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

1-(oxiran-2-yl)-N-((oxoboryl)methylene)-2-phenylethanamine (1.61 mmol, 424 mg) and benzyl 4-(aminomethyl)piperidine-1-carboxylate (1.94 nmnol, 480 mg) in isopropanol (20 mL) was heated at 80° C. for overnight. Evaporated the solvent and purified by flash chromatography to get benzyl 4-((2-hydroxy-3-((oxoboryl)methyleneamino)-4-phenylbutylamino)methyl)piperidine-1-carboxylate (880 mg). 1H NMR (300 MHz, CDCl3), δ: 7.363-7.174 (m, 10H), 5.118 (s, 2H), 4.767 (br, 1H), 4.187 (m, 2H), 3.786 (m, 1H), 3.458 (m, 1H), 3.023-2.671 (m, 6H), 2.484 (d, J=6.6 Hz, 2H), 1.733 (m, 2H), 1.600 (m, 1H), 1.347 (s, 9H), 1.135 (m, 2H).

Workup

  1. customEvaporated the solvent
  2. custompurified by flash chromatography

Sources & evidence

ORD record
ord-849eb0be731b49e3a6ea4f7a033fdcef
Source dataset
uspto-grants-2009_03
Patent number
US07504420B2

Reaction notes

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