O-(Tetrahydropyran-2-yl)hydroxylamine → HCID 76652338, compound

HRID 1666943Notes

Reaction equation

HRID 1666943 reaction equation
[CH2:1]([CH:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:23])[C:15]([CH2:17][CH:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1)=[CH2:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH:25]1[O:30][NH2:31]>>[CH2:1]([CH:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:23])[CH:15]([CH2:17][CH:18]1[CH2:19][CH2:20][CH2:21][CH2:22]1)[CH2:16][NH:31][O:30][CH:25]1[CH2:26][CH2:27][CH2:28][CH2:29][O:24]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 67140565HCID 67140565, compound

Product 1

HCID 76652338HCID 76652338, compoundYield 69%

Conditions

Temperature
45 °C

Procedure

4-Benzyl-3-(2-cyclopentylmethyl-acryloyl)-oxazolidin-2-one (22.90 g, 73.1 mmol) and O-(tetrahydro-2H-pyran-2-yl)-hydroxylamine (34.24 g, 292.3 mmol) is combined at stirred at 45° C. for 48 hours under nitrogen. The crude product is purified by flash chromatography (SiO2, 0→30% EtOAc in hexane), which gives 4-benzyl-3-[2-cyclopentylmethyl-3-(tetrahydro-pyran-2-yloxyamino)-propionyl]-oxazolidin-2-one (21.65 g, 69% yield) as an oil.

Workup

  1. customThe crude product is purified by flash chromatography (SiO2, 0→30% EtOAc in hexane), which

Sources & evidence

ORD record
ord-0cff11e6d0c64ad7a6779c0d648f0561
Source dataset
uspto-grants-2011_10
Patent number
US08044199B2

Reaction notes

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