Benzyl Bromide → HCID 178454070, compound

HRID 1445358Notes

Reaction equation

O1CCCC1.[C:6]([O:10][C:11]([NH:13][C@H:14]1[CH2:19][CH2:18][C@H:17]([OH:20])[CH2:16][CH2:15]1)=[O:12])([CH3:9])([CH3:8])[CH3:7].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[H-].[Na+]>O.CS(C)=O>[C:6]([O:10][C:11]([NH:13][C@H:14]1[CH2:15][CH2:16][C@H:17]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:18][CH2:19]1)=[O:12])([CH3:9])([CH3:7])[CH3:8]

Participants

Conditions

Temperature: 70 °C

Procedure

To 6 mL of a tetrahydrofuran solution containing 1.0 g of trans-4-(tert-butoxycarbonylamino)cyclohexanol and 873 mg of benzylbromide was gradually added 204 mg of 60% sodium hydride, 0.5 mL of dimethyl sulfoxide was then further added thereto, and the mixture was stirred at 70° C. for 2 hours. The reaction mixture was poured into water and extracted with chloroform. The extract was washed with water and brine, dried over anhydrous sodium-sulfate, and the solvent was removed under reduced pressure. The residue was applied to silica gel column chromatography (solvent: hexane-ethyl acetate (4:1)), and the obtained powdery crystals were suspended in an ethyl acetate-hexane mixed solvent, and collected by filtration to obtain trans-1-tert-butoxycarbonylamino-4-(benzyloxy)cyclohexane.

Workup

additionwas then further added
extractionextracted with chloroform
washThe extract was washed with water and brine
dry with materialdried over anhydrous sodium-sulfate
customthe solvent was removed under reduced pressure
filtrationcollected by filtration

Sources & evidence

ORD record: ord-09e5f3a1f2a64c64ab03a6d4b76d8837
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07666869B2

Reaction notes

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