Butyl iodide → HCID 178450583, compound

HRID 500073Notes

Reaction equation

[H-].[Na+].[OH:3][C@H:4]1[CH2:9][CH2:8][C@H:7]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:6][CH2:5]1.[CH2:18](I)[CH2:19][CH2:20][CH3:21].[Cl-].[NH4+]>CN(C)C=O>[CH2:18]([O:3][C@H:4]1[CH2:9][CH2:8][C@H:7]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:14])([CH3:16])[CH3:15])[CH2:6][CH2:5]1)[CH2:19][CH2:20][CH3:21]

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of 60% sodium hydride (168 mg) and anhydrous N,N-dimethylformamide (25 ml) under ice-cooling was added t-butyl trans-4-hydroxycyclohexyl-carbamate (600 mg). The mixture was stirred for 5 minutes, then butyl iodide (821 mg) was added thereto and the mixture was stirred for 3 hours under heating at 80° C. Saturated aqueous ammonium chloride was added to the reaction mixture. The mixture was extracted with toluene, and the organic layer was washed with brine, dried over sodium sulfate, and then the solvent was removed in vacuo. The residue was purified by a silica gel chromatography (eluent: gradient from 100% hexane/0% ethyl acetate to 0% hexane/100% ethyl acetate) to give 630 mg of t-butyl (trans-4-butoxycyclohexyl)carbamate.

Workup

temperaturecooling
stirringthe mixture was stirred for 3 hours
extractionThe mixture was extracted with toluene
washthe organic layer was washed with brine
dry with materialdried over sodium sulfate
customthe solvent was removed in vacuo
customThe residue was purified by a silica gel chromatography (eluent: gradient from 100% hexane/0% ethyl acetate to 0% hexane/100% ethyl acetate)

Sources & evidence

ORD record: ord-0a9078c91f4d413e8380a8fd7348a051
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07767854B2

Reaction notes

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