Sodium Carbonate → 4-Oxo-3-[(phenoxyacetyl)amino]-1-piperidinecarboxylic acid 1,1-dimethylethyl ester

HRID 1529559Notes

Reaction equation

CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH3:23][C:24]([O:27][C:28]([N:30]1[CH2:35][CH2:34][CH:33]([OH:36])[CH:32]([NH:37][C:38](=[O:47])[CH2:39][O:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH2:31]1)=[O:29])([CH3:26])[CH3:25].C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[CH3:26][C:24]([O:27][C:28]([N:30]1[CH2:35][CH2:34][C:33](=[O:36])[CH:32]([NH:37][C:38](=[O:47])[CH2:39][O:40][C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH2:31]1)=[O:29])([CH3:23])[CH3:25]

Participants

Conditions

Temperature: 80 °C

Procedure

Dess-Martin periodinane (0.53 g, 1.25 mmol) was added to a stirred solution of 4-hydroxy-3-[(phenoxyacetyl)amino]-1-piperidinecarboxylic acid 1,1-dimethylethyl ester (0.36 g, 1.0 mmol) in DCM (4 mL). The mixture was stirred at 80° C. for 5 minutes under microwave irradiation and a saturated solution of Na2CO3 was added. The organic layer was separated, dried (Na2SO4), filtered and the solvent evaporated in vacuo to yield 4-oxo-3-[(phenoxyacetyl)amino]-1-piperidinecarboxylic acid 1,1-dimethylethyl ester (0.36 g, 100% yield, 28% pure) that was used in the next step without further purification. C18H24N2O5 LCMS: Rt 2.55, m/z 249 [M+H-BOC]+ (using method, LC-MS Method 3).

Workup

customThe organic layer was separated
dry with materialdried (Na2SO4)
filtrationfiltered
customthe solvent evaporated in vacuo

Sources & evidence

ORD record: ord-4011918024e24e218bb52d62bc184182
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090632B2

Reaction notes

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