Piperidine → HCID 59287821, compound

HRID 1776966Notes

Reaction equation

HRID 1776966 reaction equation
C1C2C(COC(=O)[NH:17][CH:18]([C:31]([O:33][CH2:34][CH2:35][CH2:36][CH2:37][O:38][N+:39]([O-:41])=[O:40])=[O:32])[CH2:19][CH2:20][CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])C3C(=CC=CC=3)C=2C=CC=1.N1CCCCC1>CC#N>[NH2:17][C@@H:18]([CH2:19][CH2:20][CH2:21][CH2:22][NH:23][C:24]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:30])[C:31]([O:33][CH2:34][CH2:35][CH2:36][CH2:37][O:38][N+:39]([O-:41])=[O:40])=[O:32]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 68588787HCID 68588787, compound

Product 1

HCID 59287821HCID 59287821, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of S)-4-(nitrooxy)butyl 1-(9H-fluoren-9-yl)-13,13-dimethyl-3,11-dioxo-2,12-dioxa-4,10-diazatetradecane-5-carboxylate (2.52 g, 4.30 mmol) in CH3CN (30 ml), piperidine (2.12 ml, 21.5 mmol) was added in the dark, the reaction was stirred at rt for 25 min. Then the mixture was concentrated to a small volume and diluted with EtOAc (150 ml) and washed with 5% aqueous NaHPO4 (2×70 ml). The organic layer was dried over sodium sulphate and concentrated under reduced pressure.

Workup

  1. concentrationThen the mixture was concentrated to a small volume
  2. additiondiluted with EtOAc (150 ml)
  3. washwashed with 5% aqueous NaHPO4 (2×70 ml)
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-91d6d357ae6542fba7d95c6584cd1b3e
Source dataset
uspto-grants-2016_02
Patent number
US09266820B2

Reaction notes

Loading…