Sodium hydride → [1-(5-Nitro-pyridin-2-yl)-azetidin-3-yloxy]-acetic acid tert-butyl ester

HRID 2236201Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:13][CH:12]([OH:14])[CH2:11]2)=[N:8][CH:9]=1)([O-:3])=[O:2].[H-].[Na+].Br[CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20]>>[C:22]([O:21][C:19](=[O:20])[CH2:18][O:14][CH:12]1[CH2:11][N:10]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=2)[CH2:13]1)([CH3:25])([CH3:24])[CH3:23]

Participants

Reactant 3

HCID 24758Sodium hydride

HCID 79177tert-Butyl bromoacetate

HCID 529372641-(5-Nitropyridin-2-yl)azetidin-3-ol

Product 1

HCID 52937265[1-(5-Nitro-pyridin-2-yl)-azetidin-3-yloxy]-acetic acid tert-butyl esterYield 75.4%

Procedure

1-(5-Nitro-pyridin-2-yl)-azetidin-3-ol (176 mg, 0.9 mmol) was treated with 60% NaH in oil (108 mg, 2.7 mmol) and tert-butyl bromoacetate (199.7 uL, 1.35 mmol) as above to yield 210 mg of a yellow solid. ES-MS calcd for C14H19N3O5 (m/e) 309.32, obsd 310.2 (M+H).

Sources & evidence

ORD record: ord-1f66a677032c41dcb925a8dea45753ed
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07714126B2

Reaction notes

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