4-Nitrophenethyl bromide → HCID 66932419, compound

HRID 2046753Notes

Reaction equation

HRID 2046753 reaction equation
[CH3:1][O:2][C:3](=[O:29])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]2[C:25](=[CH:26][CH:27]=1)[O:24][C:11]1([CH2:16][CH2:15][N:14]([C:17](OC(C)(C)C)=O)[CH2:13][CH2:12]1)[CH2:10][C:9]2=[O:28].BrC[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=1>>[CH3:1][O:2][C:3](=[O:29])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]2[C:25](=[CH:26][CH:27]=1)[O:24][C:11]1([CH2:16][CH2:15][N:14]([CH2:17][CH2:32][C:33]3[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=3)[CH2:13][CH2:12]1)[CH2:10][C:9]2=[O:28]

Participants

3

Reactant 2

HCID 792664-Nitrophenethyl bromideHCID 52952087(E)-3-{1'-tert-butoxycarbonyl-4-oxo-spiro[chromane-2,4'-piperidine]-6-yl}-acrylic acid methyl ester2×

Product 1

HCID 66932419HCID 66932419, compoundYield 93.2%

Procedure

(E)-3-{4-Oxo-spiro[chromane-2,4′-piperidine]-6-yl}-acrylic acid methyl ester (337 mg, 1.00 mmol, Intermediate 1, hydrochloride salt) was alkylated using 1-(2-bromo-ethyl)-4-nitro-benzene (460 mg, 2 mmol) as described in Example 56, Step A, giving (E)-3-{1′-[2-(4-nitro-phenyl)-ethyl]-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-acrylic acid methyl ester (420 mg) as a light brown solid.

Sources & evidence

ORD record
ord-fe2894bf9a9a431582cc0e3e4bd6e3fa
Source dataset
uspto-grants-2013_11
Patent number
US08592444B2

Reaction notes

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