Sodium hydride → HCID 59301394, compound

HRID 2236202Notes

Reaction equation

HRID 2236202 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:14][CH2:13][CH:12]([OH:15])[CH2:11]2)=[N:8][CH:9]=1)([O-:3])=[O:2].[H-].[Na+].Br[CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]>>[C:23]([O:22][C:20](=[O:21])[CH2:19][O:15][CH:12]1[CH2:13][CH2:14][N:10]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=2)[CH2:11]1)([CH3:26])([CH3:25])[CH3:24]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 62916798HCID 62916798, compound

Product 1

HCID 59301394HCID 59301394, compoundYield 53.5%

Procedure

1-(5-Nitro-pyridin-2-yl)-pyrrolidin-3-ol (340 mg, 1.62 mmol) was treated with 60% NaH in oil (130 mg, 3.25 mmol) and tert-butyl bromoacetate (1.2 mL, 8.13 mmol) as above to yield 280 mg of a yellow solid following flash chromatography. ES-MS calcd for C15H21N3O5 (m/e) 323.35, obsd 324.1 (M+H).

Sources & evidence

ORD record
ord-7b4fa1c19b5d46f3923af0bf5f1e3215
Source dataset
uspto-grants-2010_05
Patent number
US07714126B2

Reaction notes

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