Propargyl alcohol → tert-butyl 2-(4-(hydroxymethyl)-1H-1,2,3-triazol-1-yl)benzylcarbamate

HRID 628681Notes

Reaction equation

HRID 628681 reaction equation
[N:1]([C:4]1[CH:18]=[CH:17][CH:16]=[CH:15][C:5]=1[CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[N+:2]=[N-:3].[CH2:19]([OH:22])[C:20]#[CH:21]>>[OH:22][CH2:19][C:20]1[N:3]=[N:2][N:1]([C:4]2[CH:18]=[CH:17][CH:16]=[CH:15][C:5]=2[CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH:21]=1

Participants

3

Reactant 2

HCID 7859Propargyl alcoholHCID 59176460Tert-butyl 2-azidobenzylcarbamate

Product 1

HCID 59176464tert-butyl 2-(4-(hydroxymethyl)-1H-1,2,3-triazol-1-yl)benzylcarbamateYield 38%

Conditions

Temperature
90 °C

Procedure

tert-butyl 2-azidobenzylcarbamate, 12, (5.4 g, 21.7 mmol) was dissolved in neat propargyl alcohol (10 mL). The reaction mixture was stirred at 90° C. for 18 h. The reaction mixture was then concentrated in vacuo and the resulting residue dissolved in diethyl ether. Upon standing, triazole 13 crystallized. The crystals were collected by filtration yielding 2.5 g (38%) of 13: 1H NMR (400 MHz, CDCl3) δ 7.82, (s, 1H), 7.64-7.35 (m, 3H), 7.34-7.30 (m, 1H), 5.35, (bs, 1H), 4.87, (s, 2H), 4.15 (s, 2H), 1.42 (s, 9H); ESI+ MS: m/z (rel intensity) 249 (100, M-tBu).

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. dissolutionthe resulting residue dissolved in diethyl ether
  3. customtriazole 13 crystallized
  4. filtrationThe crystals were collected by filtration

Sources & evidence

ORD record
ord-5bc6d28841cf4226b05ef31d332fb685
Source dataset
uspto-grants-2016_04
Patent number
US09314468B2

Reaction notes

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