Tert-butyl 3-oxopyrrolidine-1-carboxylate → tert-Butyl 3-methylidenepyrrolidine-1-carboxylate

HRID 2040853Notes

Reaction equation

HRID 2040853 reaction equation
[CH2:1]=C1CCN(C2C([N+]([O-])=O)=CC=CN=2)CC1.[C:17]([N:24]1[CH2:28][CH2:27][C:26](=O)[CH2:25]1)([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18]>>[CH2:1]=[C:26]1[CH2:27][CH2:28][N:24]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:25]1

Participants

3

Reactant 2

HCID 471360Tert-butyl 3-oxopyrrolidine-1-carboxylateHCID 574938092-(4-Methylene-1-piperidyl)-3-nitropyridine

Product 1

HCID 15297967tert-Butyl 3-methylidenepyrrolidine-1-carboxylate

Procedure

The title compound was synthesised following the method described here for Compound 2a using 1-Boc-3-pyrrolidinone instead of 1-(3-nitro-2-pyridyl)-4-oxopiperidine. After the usual work-up procedure, the crude product was purified by automated flash chromatography (Horizon®TM-Biotage) eluting with a Petroleum Ether-EtOAc gradient from 95:5 to 7:3, yielding the title compound as brownish oil. Yield: 75.8%.

Workup

  1. customThe title compound was synthesised
  2. customAfter the usual work-up procedure, the crude product was purified by automated flash chromatography (Horizon®TM-Biotage)
  3. washeluting with a Petroleum Ether-EtOAc gradient from 95:5 to 7:3

Sources & evidence

ORD record
ord-4124b675ff494923995d5d1e4b097df0
Source dataset
uspto-grants-2013_11
Patent number
US08580962B2

Reaction notes

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