Triethylamine → Pentylcarbamic acid 4-hydroxymethyl-5-oxo-2,3,4,5-tetrahydrobenzo[b]oxepin-4-ylmethyl ester

HRID 2265823Notes

Reaction equation

HRID 2265823 reaction equation
[OH:1][CH2:2][C:3]1([CH2:15][OH:16])[CH2:9][CH2:8][O:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[C:4]1=[O:14].C(N(CC)CC)C.[CH2:24]([N:29]=[C:30]=[O:31])[CH2:25][CH2:26][CH2:27][CH3:28]>O1CCCC1>[OH:16][CH2:15][C:3]1([CH2:2][O:1][C:30](=[O:31])[NH:29][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:9][CH2:8][O:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[C:4]1=[O:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 206036Pentane, 1-isocyanato-HCID 670731254,4-Bis(hydroxymethyl)-3,4-dihydro-2H-benzo[b]oxepin-5-one

Product 1

HCID 11964818Pentylcarbamic acid 4-hydroxymethyl-5-oxo-2,3,4,5-tetrahydrobenzo[b]oxepin-4-ylmethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4,4-bis(hydroxymethyl)-3,4-dihydro-2H-benzo[b]oxepin-5-one (260 mg, 1.17 mmol) in 15 ml of tetrahydrofuran were added, at room temperature, triethylamine (0.18 ml, 1.3 mmol) and n-pentyl isocyanate (332 μl, 2.57 mmol). The mixture was heated to reflux for 24 hours, concentrated and purified by column chromatography on silica gel (eluent: 1:2 ethyl acetate/hexane). The product was obtained in a yield of 210 mg (54%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 24 hours
  3. concentrationconcentrated
  4. custompurified by column chromatography on silica gel (eluent: 1:2 ethyl acetate/hexane)
  5. customThe product was obtained in a yield of 210 mg (54%)

Sources & evidence

ORD record
ord-7f520a256ec9423eacb3bb90cac41eb6
Source dataset
uspto-grants-2010_12
Patent number
US07858613B2

Reaction notes

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