1-Bromopentane → Tert-butyl (pentyloxy)carbamate

HRID 1258570Notes

Reaction equation

HRID 1258570 reaction equation
[OH:1][NH:2][C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].Br[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].C1CCN2C(=NCCC2)CC1>CC#N>[C:5]([O:4][C:3](=[O:9])[NH:2][O:1][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])([CH3:8])([CH3:7])[CH3:6]

Participants

5

Reactant 3

HCID 80571-BromopentaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 97534tert-butyl N-hydroxycarbamate

Product 1

HCID 86653126Tert-butyl (pentyloxy)carbamateYield 100.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Tert-butyl hydroxycarbamate (2.1 g, 15.77 mmol, 1 eq.) was dissolved in MeCN and bromopentane (2.73 g, 18.13 mmol, 1.15 eq.) was added followed by DBU (2.52 g, 16.56 mmol, 1.05 eq.). The reaction was stirred at room temperature for 12 h and quenched with 0.1N HCl, extracted with EtOAc, dried over MgSO4, and concentrated. The residue was purified by chromatography on silica gel to give tert-butyl(pentyloxy)carbamate (3.23 g, 91% yield) as a clear oil.

Workup

  1. customquenched with 0.1N HCl
  2. extractionextracted with EtOAc
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-ca8a533c5454482184dfe932440e6a85
Source dataset
uspto-grants-2013_06
Patent number
US08466176B2

Reaction notes

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