tert-Butyl (2S)-2-(aminomethyl)piperidine-1-carboxylate → HCID 58874493, compound

HRID 2217936Notes

Reaction equation

HRID 2217936 reaction equation
F[C:2]1[CH:20]=[CH:19][C:5]([C:6]([N:8]([CH2:14][C:15]([F:18])([F:17])[F:16])[CH2:9][C:10]([F:13])([F:12])[F:11])=[O:7])=[CH:4][C:3]=1[N+:21]([O-:23])=[O:22].[NH2:24][CH2:25][C@@H:26]1[CH2:31][CH2:30][CH2:29][CH2:28][N:27]1[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33]>CCO>[F:11][C:10]([F:12])([F:13])[CH2:9][N:8]([CH2:14][C:15]([F:16])([F:18])[F:17])[C:6]([C:5]1[CH:19]=[CH:20][C:2]([NH:24][CH2:25][C@@H:26]2[CH2:31][CH2:30][CH2:29][CH2:28][N:27]2[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[C:3]([N+:21]([O-:23])=[O:22])[CH:4]=1)=[O:7]

Participants

4

Reactant 2

HCID 1502020tert-Butyl (2S)-2-(aminomethyl)piperidine-1-carboxylateHCID 589117444-Fluoro-3-nitro-N,N-bis(2,2,2-trifluoroethyl)benzamide

Product 1

HCID 58874493HCID 58874493, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Following the general procedure for Intermediate 2 using 4-fluoro-3-nitro-N,N-bis(2,2,2-trifluoroethyl)benzamide (200 mg, 0.574 mmol) and tert-butyl (2S)-2-(aminomethyl)piperidine-1-carboxylate (150 mg, 0.689 mmol) in 10 mL of EtOH containing TEA (0.120 mL, 0.861 mmol). The product was purified by flash chromatography on silica gel using 3:1/hexanes:EtOAc as eluent Yield: 311 mg (99%); 1H NMR (400 MHz, CHLOROFORM-D) δ 1.47 (s, 9H), 1.52 (m, 1H), 1.66 (m, 1H), 1.71 (s, 2H), 1.74 (s, 2H), 2.79 (m, 1H), 3.36 (m, 1H), 3.65 (m, 1H), 4.09 (s, 1H), 4.26 (q, J=8.33 Hz, 4H), 4.64 (m, 1H), 7.07 (d, J=8.98 Hz, 1H), 7.55 (dd, J=8.89, 2.05 Hz, 1H), 8.30 (d, J=2.15 Hz, 1H), 8.39 (m, 1H); MS (ESI) 542.81 (MH+).

Workup

  1. customThe product was purified by flash chromatography on silica gel using 3:1/hexanes

Sources & evidence

ORD record
ord-c1bf882043554de7a1cb739767ca39f3
Source dataset
uspto-grants-2008_08
Patent number
US07407968B2

Reaction notes

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