Triethylamine → Methyl 5-(9-(3-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecane-4-carbonyl)thiophene-2-carboxylate

HRID 471032Notes

Reaction equation

HRID 471032 reaction equation
FC(F)(F)C(O)=O.[O:8]1[C:13]2([CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH2:12][N:11]([C:19]([C:21]2[S:25][C:24]([C:26]([O:28][CH3:29])=[O:27])=[CH:23][CH:22]=2)=[O:20])[CH2:10][CH2:9]1.Br[CH2:31][C:32]1[CH:33]=[C:34]([CH2:38][CH2:39][OH:40])[CH:35]=[CH:36][CH:37]=1.C(N(CC)CC)C>C(#N)C>[OH:40][CH2:39][CH2:38][C:34]1[CH:33]=[C:32]([CH:37]=[CH:36][CH:35]=1)[CH2:31][N:16]1[CH2:17][CH2:18][C:13]2([O:8][CH2:9][CH2:10][N:11]([C:19]([C:21]3[S:25][C:24]([C:26]([O:28][CH3:29])=[O:27])=[CH:23][CH:22]=3)=[O:20])[CH2:12]2)[CH2:14][CH2:15]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 18999576Benzeneethanol, 3-(bromomethyl)-HCID 67292236Methyl 5-(1-oxa-4,9-diazaspiro[5.5]undecane-4-carbonyl)thiophene-2-carboxylate trifluoroacetate

Product 1

HCID 57989150Methyl 5-(9-(3-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecane-4-carbonyl)thiophene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
20 °C

Procedure

A solution of methyl 5-(1-oxa-4,9-diazaspiro[5.5]undecane-4-carbonyl)thiophene-2-carboxylate trifluoroacetate (example 30, step b) (0.46 g) and 2-(3-(bromomethyl)phenyl)ethanol (example 6, step a) (0.226 g) in acetonitrile (10 mL) was treated with triethylamine (0.44 mL) and the mixture stirred at 20° C. for 2 hours. The solvent was evaporated under reduced pressure and the residue partitioned between ethyl acetate and saturated sodium bicarbonate solution. The organic layer was dried over sodium sulphate, filtered and the solvent evaporated under reduced pressure. The crude product was purified by flash silica chromatography using 1% triethylamine and 3% methanol in dichloromethane as solvent. Pure fractions were evaporated to dryness to afford the subtitled compound. Yield 0.41 g.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue partitioned between ethyl acetate and saturated sodium bicarbonate solution
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. filtrationfiltered
  5. customthe solvent evaporated under reduced pressure
  6. customThe crude product was purified by flash silica chromatography
  7. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-1b04b597b15f4200869e22e5b71dd5d7
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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