tert-Butyl 4-oxopiperidine-1-carboxylate → tert-Butyl 7-bromo-4-oxo-3,4-dihydro-1'H-spiro[1-benzopyran-2,4'-piperidine]-1'-carboxylate

HRID 518149Notes

Reaction equation

HRID 518149 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([OH:11])[CH:3]=1.[C:12]([N:19]1[CH2:24][CH2:23][C:22](=O)[CH2:21][CH2:20]1)([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].COC(=O)/C=C/C1C=C2C(=CC=1)OC1(CCNCC1)CC2=O>>[C:15]([O:14][C:12]([N:19]1[CH2:24][CH2:23][C:22]2([CH2:9][C:8](=[O:10])[C:5]3[C:4](=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=3)[O:11]2)[CH2:21][CH2:20]1)=[O:13])([CH3:18])([CH3:16])[CH3:17]

Participants

4

Reactant 3

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 107274031-(4-Bromo-2-hydroxyphenyl)ethan-1-oneHCID 52952093(E)-3-{4-oxo-spiro[chromane-2,4'-piperidine]-6-yl}-acrylic acid methyl ester

Product 1

HCID 27281806tert-Butyl 7-bromo-4-oxo-3,4-dihydro-1'H-spiro[1-benzopyran-2,4'-piperidine]-1'-carboxylate

Procedure

1-(4-Bromo-2-hydroxy-phenyl)ethanone (10.1 g, 47.0 mmol) was coupled with N—BOC-4-piperidone according to the procedure for preparation of Intermediate 1, Step A, giving 7-bromo-4-oxo-spiro[chromane-2,4′-piperidine]-1′-carboxylic acid tert-butyl ester (18 g) as an orange solid.

Sources & evidence

ORD record
ord-e8bf3eed038c457bb2e79c7ba628d05f
Source dataset
uspto-grants-2015_08
Patent number
US09115148B2

Reaction notes

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