Benzyl Bromide → HCID 178454070, compound

HRID 722027Notes

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-ce6fada85e99472a97842df9954cd253
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07138397B2

Reaction notes

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