Ammonia → HCID 66692768, compound

HRID 2367995Notes

Reaction equation

HRID 2367995 reaction equation
[Cl:1][C:2]1[C:10]2[CH:9]([CH2:11][N+:12]([O-])=O)[O:8][B:7]([OH:15])[C:6]=2[C:5]([O:16][CH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:4][CH:3]=1.N>CCO.[Ni]>[NH2:12][CH2:11][CH:9]1[O:8][B:7]([OH:15])[C:6]2[C:5]([O:16][CH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[CH:4][CH:3]=[C:2]([Cl:1])[C:10]1=2

Participants

5

Reactant 2

HCID 222AmmoniaHCID 66694000HCID 66694000, compound

Product 1

HCID 66692768HCID 66692768, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent2×

Procedure

A mixture of tert-butyl 3-(4-chloro-1-hydroxy-3-(nitromethyl)-1,3-dihydrobenzo[c][1,2]oxaborol-7-yloxy)propylcarbamate (480 mg, 1.2 mmol), Raney-Ni (500 mg) and 2 M NH3 in EtOH (3 mL) in EtOH (15 mL) was shaken under an atmosphere of H2 for 2 h at room temperature. The mixture was filtered through a bed of Celite and the filtrate was concentrated in vacuo. The resulting solid was used directly for the next step.

Workup

  1. filtrationThe mixture was filtered through a bed of Celite
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-d841ae9c1ce84b16aaad35aa68b5921c
Source dataset
uspto-grants-2014_04
Patent number
US08703742B2

Reaction notes

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