Ethanol → HCID 131734234, compound

HRID 1498978Notes

Reaction equation

HRID 1498978 reaction equation
[C:1]([NH:4][C@@:5]1([C:26]([NH:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:9][C@@H:8]([CH2:10][N+:11]([O-])=O)[CH2:7][C@@H:6]1[CH2:14][CH2:15][CH2:16][B:17]1[O:21][C:20]([CH3:23])([CH3:22])[C:19]([CH3:25])([CH3:24])[O:18]1)(=[O:3])[CH3:2].C(OCC)(=O)C.C(O)C>O1CCCC1.[Ni]>[C:1]([NH:4][C@@:5]1([C:26]([NH:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:9][C@@H:8]([CH2:10][NH2:11])[CH2:7][C@@H:6]1[CH2:14][CH2:15][CH2:16][B:17]1[O:21][C:20]([CH3:23])([CH3:22])[C:19]([CH3:24])([CH3:25])[O:18]1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 702EthanolHCID 8857Ethyl AcetateHCID 131734235HCID 131734235, compound

Product 1

HCID 131734234HCID 131734234, compoundYield 99.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of (1S,2S,4S)-1-acetamido-N-(tert-butyl)-4-(nitromethyl)-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl)cyclopentanecarboxamide (0.907 g, 2.0 mmol) in a mixture of tetrahydrofuran (20 mL), ethyl acetate (15 mL), and ethanol (5 mL) under nitrogen was added Raney nickel (1.2 g). The reaction mixture was then purged with hydrogen and stirred under an atmosphere of hydrogen at room temperature for 6 h. At the end of this period, the mixture was purged with nitrogen, then carefully through Celite®. After rinsing the filter cake with ethyl acetate the combined filtrate was concentrated in vacuo to afford the subject compound (0.841 g, 99%) as a white solid. NMR (CDCl3): δ 6.98 (br s, 1 H), 6.93 (br s, 1 H), 2.55-2.70 (m, 3 H), 2.44 (m, 1 H), 2.24 (m, 1 H), 1.91 (m, 3 H), 1.50-1.65 (m, 3 H), 1.20-1.45 (m, 4 H), 1.26 (s, 9 H), 1.66 (s, 12 H), 0.60-0.75 (m, 2 H). MS (M+1): 424.4.

Workup

  1. customThe reaction mixture was then purged with hydrogen
  2. customAt the end of this period, the mixture was purged with nitrogen
  3. washAfter rinsing the filter cake with ethyl acetate the combined filtrate
  4. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-9fb459cf19ba4f62a5b2ae3889b7f445
Source dataset
uspto-grants-2015_12
Patent number
US09200011B2

Reaction notes

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