Allyl bromide → [4-(4-Allyloxyphenyl)butyl]carbamic acid benzyl ester

HRID 217906Notes

Reaction equation

HRID 217906 reaction equation
[CH3:1][C:2](C)([O-])[CH3:3].[K+].[C:7]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1)([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8].C(Br)C=C>CC#N.C1OCCOCCOCCOCCOCCOC1>[C:7]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:3][CH:2]=[CH2:1])=[CH:24][CH:23]=1)([O:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:8]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 11637991N-Cbz4-(4-hydroxyphenyl)butylamineHCID 23665647Potassium tert-butoxide

Product 1

HCID 11551825[4-(4-Allyloxyphenyl)butyl]carbamic acid benzyl esterYield 71%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 6342AcetonitrileSolvent2×

Procedure

Potassium tert-butoxide (1.7 g, 15.2 mmol) and 18-crown-6 (0.1 g, 0.3 mmol) were added to a solution of 29 (4.3 g, 14.3 mmol) in dry MeCN (80 mL) and the mixture was stirred for 20 min at room temperature. After this time, allyl bromide (1.2 mL, 14.3 mmol) in MeCN (10 mL) was added. The reaction mixture was stirred overnight at room temperature, then the precipitate was filtered off and washed with ethyl acetate. The organic fractions were combined, the solvent was removed at reduced pressure and the residue was purified twice by flash chromatography (silica gel, 1:1 ethyl acetate/hexanes) to provide compound 30 (3.4 g, 71%) as a white solid. 1H NMR (300 MHz, CDCl3) δ 1.55 (m, 4H), 2.54 (t, 2H), 3.20 (m, 2H), 4.50 (d, 2H), 5.08 (s, 2H), 5.28 (d, 1H), 5.40 (d, 1H), 6.06 (m, 1H), 6.82 (d, 2H), 7.05 (d, 2H), 7.33 (s, 5H)

Workup

  1. stirringThe reaction mixture was stirred overnight at room temperature
  2. filtrationthe precipitate was filtered off
  3. washwashed with ethyl acetate
  4. customthe solvent was removed at reduced pressure
  5. customthe residue was purified twice by flash chromatography (silica gel, 1:1 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-bdf08aadcb73461c9820dea18646ebef
Source dataset
uspto-grants-2012_06
Patent number
US08198286B2

Reaction notes

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