Water → HCID 68508231, compound

HRID 1715111Notes

Reaction equation

[CH2:1]([O:4][C:5](=[O:16])[C:6]1[CH:11]=[CH:10][C:9](F)=[C:8]([N+:13]([O-:15])=[O:14])[CH:7]=1)[CH:2]=[CH2:3].[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH:27]([NH2:30])[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18].C(N(C(C)C)C(C)C)C.O>CN(C=O)C>[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH:27]([NH:30][C:9]2[CH:10]=[CH:11][C:6]([C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:16])=[CH:7][C:8]=2[N+:13]([O-:15])=[O:14])[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:18])[CH3:19]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 4-fluoro-3-nitro-benzoic acid allyl ester (84.3 g, 0.37 mol, 1.0 equiv) and 4-amino-piperidine-1-carboxylic acid tert-butyl ester (75.0 g, 0.37 mol, 1.0 equiv; commercially available) in DMF (500 mL) was added N-ethyldiisopropylamine (111.3 g, 0.86 mol, 2.3 equiv) and the reaction mixture heated at 70° C. for 6 h. The reaction mixture was cooled, poured into water (2 L) and the resulting mixture stirred at rt for 1 h. The precipitate was filtered, washed with water and hexane and finally dried over MgSO4 to obtain 129.1 g (85%) of the title compound. 1H NMR (400 MHz, DMSO): δ 1.46 (s, 9H), 1.46-1.56 (m, 2H), 1.92-1.98 (m, 2H), 2.90-2.98 (m, 2H), 3.88-3.95 (m, 3H), 4.78 (d, J=5.2 Hz, 2H), 5.27 (d, J=10.4 Hz, 1H), 5.38 (d, J=17.3 Hz, 1H), 6.00-6.06 (m, 1H), 7.29 (d, J=9.2 Hz, 1H), 7.99 (dd, J=9.2 Hz, J=1.6 Hz, 1H), 8.24 (d, J=7.8 Hz, 1H), 8.64 (s, 1H).

Workup

temperatureThe reaction mixture was cooled
filtrationThe precipitate was filtered
washwashed with water and hexane
dry with materialfinally dried over MgSO4

Sources & evidence

ORD record: ord-1cf0fac99bd442f8805608f6942698a5
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07799806B2

Reaction notes

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