Piperidine → HCID 59287454, compound

HRID 1776968Notes

Reaction equation

HRID 1776968 reaction equation
[N+:1]([O:4][CH2:5][CH2:6][CH2:7][C:8]([O:10][CH2:11][CH:12]([NH:20]C(OCC1C2C=CC=CC=2C2C1=CC=CC=2)=O)[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:9])([O-:3])=[O:2].N1CCCCC1>CC#N>[N+:1]([O:4][CH2:5][CH2:6][CH2:7][C:8]([O:10][CH2:11][CH:12]([NH2:20])[C:13]([O:15][C:16]([CH3:18])([CH3:17])[CH3:19])=[O:14])=[O:9])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 68590767HCID 68590767, compound

Product 1

HCID 59287454HCID 59287454, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-tert-butoxy-3-oxopropyl 4-(nitrooxy)butanoate 1.26 g, 2.45 mmol) in CH3CN (15 ml), piperidine (1.21 ml, 12.2 mmol) was added in the dark, the reaction was stirred at room temperature for 25 min. Then the mixture was concentrated to a small volume and diluted with EtOAc (80 ml) and washed with 5% aqueous NaHPO4. The organic layer was dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by flash chromatography (CH2Cl2/MeOH 98:2 as eluent) yielding the title compound (0.500 g, 70%).

Workup

  1. concentrationThen the mixture was concentrated to a small volume
  2. additiondiluted with EtOAc (80 ml)
  3. washwashed with 5% aqueous NaHPO4
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography (CH2Cl2/MeOH 98:2 as eluent)

Sources & evidence

ORD record
ord-01fcb56aa12d4c93982a1fcf41b8b501
Source dataset
uspto-grants-2016_02
Patent number
US09266820B2

Reaction notes

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