Triethylamine → (2-hydroxy-ethyl)-(1H-indol-7-ylmethyl)-carbamic acid benzyl ester

HRID 405900Notes

Reaction equation

HRID 405900 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[CH2:10][NH:11][CH2:12][CH2:13][OH:14])[CH:3]=[CH:2]1.C(N(CC)CC)C.Cl[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24]>ClCCCl>[CH2:26]([O:25][C:23](=[O:24])[N:11]([CH2:12][CH2:13][OH:14])[CH2:10][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[NH:1][CH:2]=[CH:3]2)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 219500502-[(1H-Indol-7-ylmethyl)amino]-ethan-1-ol

Product 1

HCID 67017088(2-hydroxy-ethyl)-(1H-indol-7-ylmethyl)-carbamic acid benzyl esterYield 52%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 2-[(1H-indol-7-ylmethyl)-amino]-ethanol (4.4 g) in 1,2-dichloroethane (40 mL) was added triethylamine (4.85 mL, 34.6 mmol) followed by benzyl chloroformate (3.57 mL, 25.34 mmol). The mixture was allowed to stir at room temperature for 2 hours. The mixture was quenched by addition of water (20 mL), and 1.0 M sodium hydroxide (10 mL). The organic layer was separated and the aqueous layer extracted with 1,2-dichloroethane (20 mL). The combined organic extracts were washed with 1.0 M hydrochloric acid (20 mL), water (20 mL), dried over anhydrous sodium sulfate and evaporated to dryness. The residue was purified by silica gel chromatography, eluting with 20% ethyl acetate in hexanes to 40% ethyl acetate in hexanes to afford (2-hydroxy-ethyl)-(1H-indol-7-ylmethyl)-carbamic acid benzyl ester (2.79 g, 52% combined yield for two steps) as a colorless oil. 1H NMR (CDCl3) 400 MHz δ: 9.97 (br s, 1H), 7.75-6.9 (m, 8H), 6.54 (br s, 1H), 5.21 (s, 2H), 4.9-4.6 (m, 3H), 3.85-3.57 (m, 2H), 3.55-3.23 (m, 3H); LCMS M+H=325.

Workup

  1. customThe mixture was quenched by addition of water (20 mL), and 1.0 M sodium hydroxide (10 mL)
  2. customThe organic layer was separated
  3. extractionthe aqueous layer extracted with 1,2-dichloroethane (20 mL)
  4. washThe combined organic extracts were washed with 1.0 M hydrochloric acid (20 mL), water (20 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated to dryness
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with 20% ethyl acetate in hexanes to 40% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-febaa344235642c697f7ad5784cfe2dc
Source dataset
uspto-grants-2014_06
Patent number
US08754078B2

Reaction notes

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