Ethyl isocyanate → Ethyl-carbamic acid 1-[2,3-dimethoxy-6-(1-oxo-indan-4-yl)-phenoxymethyl]-cyclopropylmethyl ester

HRID 2171020Notes

Reaction equation

[OH:1][CH2:2][C:3]1([CH2:6][O:7][C:8]2[C:13]([O:14][CH3:15])=[C:12]([O:16][CH3:17])[CH:11]=[CH:10][C:9]=2[C:18]2[CH:26]=[CH:25][CH:24]=[C:23]3[C:19]=2[CH2:20][CH2:21][C:22]3=[O:27])[CH2:5][CH2:4]1.C(N(CC)CC)C.[CH2:35]([N:37]=[C:38]=[O:39])[CH3:36]>ClCCl>[CH3:15][O:14][C:13]1[C:12]([O:16][CH3:17])=[CH:11][CH:10]=[C:9]([C:18]2[CH:26]=[CH:25][CH:24]=[C:23]3[C:19]=2[CH2:20][CH2:21][C:22]3=[O:27])[C:8]=1[O:7][CH2:6][C:3]1([CH2:2][O:1][C:38](=[O:39])[NH:37][CH2:35][CH3:36])[CH2:4][CH2:5]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirring solution of 4-[2-(1-Hydroxymethyl-cyclopropylmethoxy)-3,4-dimethoxy-phenyl]-indan-1-one (Compound 177) (150 mg, 0.407 mmol) in dichloromethane (15 mL), were added triethylamine (123 mg, 1.22 mmol) and ethyl isocyanate (86 mg, 1.22 mmol) and the resultant reaction mixture was heated to 50° C. for 16 h. The reaction mixture was quenched with sodium bicarbonate solution and extracted with dichloromethane (3×). The combined dichloromethane layer was washed with brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure. Purification by column chromatography (silica gel, 0-30% ethyl acetate in pet ether) afforded the title compound as a solid.

Workup

customthe resultant reaction mixture
customThe reaction mixture was quenched with sodium bicarbonate solution
extractionextracted with dichloromethane (3×)
washThe combined dichloromethane layer was washed with brine
dry with materialdried over anhydrous sodium sulphate
concentrationconcentrated under reduced pressure
customPurification by column chromatography (silica gel, 0-30% ethyl acetate in pet ether)

Sources & evidence

ORD record: ord-d0803b1a09674cf381185a7388a19624
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09051290B2

Reaction notes

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