Pyrrolidine → HCID 68753644, compound

HRID 1753971Notes

Reaction equation

[Cl:1][C:2]1[C:3]([OH:11])=[C:4]([C:8](=O)[CH3:9])[CH:5]=[CH:6][CH:7]=1.C([N:19]1[CH2:24][CH2:23][C:22](=O)[CH2:21][CH2:20]1)(OC(C)(C)C)=O.N1CCCC1>C1(C)C(C)=CC=CC=1>[Cl-:1].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[O:11][C:22]1([CH2:23][CH2:24][NH2+:19][CH2:20][CH2:21]1)[CH2:9][CH2:8]2

Participants

Conditions

Temperature: 100 °C

Procedure

tert-Butyl 8-chloro-4-oxo-3,4-dihydro-1′H-spiro[chromene-2,4′-piperidine]-1′-carboxylate A mixture of 1-(3-chloro-2-hydroxyphenyl)ethanone (500 mg, 2.93 mmol), 1-boc-4-piperidone (584 mg, 2.93 mmol) and pyrrolidine (61 pt, 0.738 mmol) in Xylene (4 mL) was heated to 100° C. for 20 h. The reaction mixture was purified by column chromatography on SiO2 (40 g, gradient from 0 to 40% EtOAc/hexanes) to afford the title compound as a white solid. LC-MS: m/z=376.1, 374.1 (M+Na).

Workup

customThe reaction mixture was purified by column chromatography on SiO2 (40 g, gradient from 0 to 40% EtOAc/hexanes)

Sources & evidence

ORD record: ord-fe7d549a87844f9a959e8c8ecb6632c9
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09168248B2

Reaction notes

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