Triethylamine → HCID 59547800, compound

HRID 510511Notes

Reaction equation

HRID 510511 reaction equation
[NH2:1][CH:2]1[CH:11]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)[C:10]2[CH:9]=[C:8]([OH:21])[CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3]1.C(N(CC)CC)C.[C:29](=O)([O:35]C(C)(C)C)[O:30][C:31]([CH3:34])([CH3:33])[CH3:32]>O1CCCC1>[Cl:20][C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][C:16]=1[Cl:19])[CH2:12][CH:11]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([OH:21])[CH:9]=2)[CH2:4][CH2:3][CH:2]1[NH:1][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 57471196HCID 57471196, compound

Product 1

HCID 59547800HCID 59547800, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7-Amino-8-(3,4-dichlorobenzyl)-5,6,7,8-tetrahydronaphthalen-2-ol (10.8 g) and triethylamine (14.01 mL, 101 mmol) were dissolved in dry tetrahydrofuran (200 mL). Di-tert-butyl carbonate (7.31 g, 33.5 mmol) was added in small portions at room temperature. The reaction mixture was stirred over night. The solvent was evaporated in vacuo. The residue was dissolved in ethyl acetate (300 mL) and washed with water (2×200 mL). The ethyl acetate solution of the crude product was dried (Na2SO4). The solvent was evaporated in vacuo and the crude product was used for the next step without further purification. Yield: 12.2 g.

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate (300 mL)
  3. washwashed with water (2×200 mL)
  4. dry with materialThe ethyl acetate solution of the crude product was dried (Na2SO4)
  5. customThe solvent was evaporated in vacuo
  6. customthe crude product was used for the next step without further purification

Sources & evidence

ORD record
ord-3e43dd45476141d4bbce3fb1a16ed1e4
Source dataset
uspto-grants-2015_08
Patent number
US09096619B2

Reaction notes

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