Triethylamine → HCID 68583241, compound

HRID 2239254Notes

Reaction equation

HRID 2239254 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH2:9][OH:10].CCN(CC)CC.[O:18](C(OC(C)(C)C)=O)[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=O>C(Cl)Cl>[C:22]([O:21][C:19](=[O:18])[NH:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH2:9][OH:10])([CH3:25])([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 5764502-Amino-5-methylbenzyl alcohol

Product 1

HCID 68583241HCID 68583241, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-amino-5-methyl-phenyl)-methanol (18.08 mmol, 2.48 g) in 50 mL CH2Cl2 was added Et3N (20 mmol, 2.8 mL) was added BOC2O and the reaction was allowed to stir overnight at r.t. for two days. The reaction mixture was washed with dilute HCl solution. The organic layer was separated, dried over Na2SO4, filtered and the solvent was removed in vacuo. (2-Hydroxymethyl-4-methyl-phenyl)-carbamic acid tert-butyl ester was obtained as a golden yellow thick oil (4.2 g) which was used in the next step without purification. MS (electrospray): mass calculated for C13H19NO3, 237.14; m/z found 238, [M+H]+.

Workup

  1. washThe reaction mixture was washed with dilute HCl solution
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-e65c90d8c2844e0c9c244c376499fbfd
Source dataset
uspto-grants-2010_05
Patent number
US07723326B2

Reaction notes

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