Di-tert-butyl dicarbonate → tert-Butyl allyl(7-cyano-1,2,3,4-tetrahydronaphthalen-2-yl)carbamate

HRID 1466052Notes

Reaction equation

HRID 1466052 reaction equation
[CH2:1]([NH:4][CH:5]1[CH2:14][C:13]2[CH:12]=[C:11]([C:15]#[N:16])[CH:10]=[CH:9][C:8]=2[CH2:7][CH2:6]1)[CH:2]=[CH2:3].[O:17](C(OC(C)(C)C)=O)[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=O>C(Cl)Cl>[CH2:1]([N:4]([CH:5]1[CH2:6][CH2:7][C:8]2[C:13](=[CH:12][C:11]([C:15]#[N:16])=[CH:10][CH:9]=2)[CH2:14]1)[C:18](=[O:17])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 895248047-(Allylamino)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

Product 1

HCID 89526338tert-Butyl allyl(7-cyano-1,2,3,4-tetrahydronaphthalen-2-yl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 7-(Allylamino)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile (300 mg, 1.4 mmol) in 20 mL of DCM was added TEA (430 mg, 4.26 mmol) and BOC2O (460 mg, 2.1 mmol), and the mixture was stirred at room temperature overnight. The reaction was completed, and DCM was added. Then the mixture was washed with water and brine, and the organic layer was dried over anhydrous Na2SO4 and concentrated to give the title compound. MS m/z: 313 [M+1]+.

Workup

  1. washThen the mixture was washed with water and brine
  2. dry with materialthe organic layer was dried over anhydrous Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-11880a7c481c42058d59cd33a89986ce
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

Loading…