Dichloromethane → HCID 66932587, compound

HRID 518234Notes

Reaction equation

HRID 518234 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([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)C.[CH2:39](Cl)Cl>>[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]([CH:17]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH3:39])[CH2:13][CH2:12]1)[CH2:10][C:9]2=[O:28]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 11454(1-Bromoethyl)benzeneHCID 52952087(E)-3-{1'-tert-butoxycarbonyl-4-oxo-spiro[chromane-2,4'-piperidine]-6-yl}-acrylic acid methyl ester2×

Product 1

HCID 66932587HCID 66932587, compoundYield 90%

Procedure

A mixture of (E)-3-{4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-acrylic acid methyl ester hydrochloride (500 mg, 1.48 mmol, Intermediate 1), TEA (0.41 ml, 2.96 mmol) and (±)-(1-bromoethyl)benzene (547 mg, 2.96 mmol) in DCM (25 ml) was stirred for 48 h at RT and then washed with brine. The organic phase was dried over Na2SO4 and evaporated. The crude residue was purified by column chromatography (eluent: from DCM to DCM/MeOH 96:4) to give (±)-(E)-3-{1′-(1-phenyl-ethyl)-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-acrylic acid methyl ester (546 mg, 90%).

Workup

  1. washwashed with brine
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customevaporated
  4. customThe crude residue was purified by column chromatography (eluent: from DCM to DCM/MeOH 96:4)

Sources & evidence

ORD record
ord-74c7e46473454677967229a11c04dc1b
Source dataset
uspto-grants-2015_08
Patent number
US09115148B2

Reaction notes

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