Triphenylphosphine → [2-(1H-indol-4-yloxy)ethyl]-methylcarbamic acid tert-butyl ester

HRID 1912773Notes

Reaction equation

HRID 1912773 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([OH:10])[C:4]=2[CH:3]=[CH:2]1.[C:11]([O:15][C:16](=[O:22])[N:17]([CH2:19][CH2:20]O)[CH3:18])([CH3:14])([CH3:13])[CH3:12].N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[C:11]([O:15][C:16](=[O:22])[N:17]([CH2:19][CH2:20][O:10][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[CH:3]=[CH:2][NH:1]2)[CH3:18])([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 754211H-indol-4-olHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 545700N-(tert-Butoxycarbonyl)-N-methyl-2-aminoethanol

Product 1

HCID 10708626[2-(1H-indol-4-yloxy)ethyl]-methylcarbamic acid tert-butyl esterYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 50 mL of tetrahydrofuran, 200 mg (1.51 mmol) of 1H-indole-4-ol and 527 mg (3.00 mmol) of 2-hydroxyethyl-methylcarbamic acid tert-butyl ester were dissolved, and 1.51 mL (3.00 mmol) of a diethyl azodicarboxylate 40% toluene solution and 788 mg (3.00 mmol) of triphenylphosphine were added thereto and the mixture solution was stirred at room temperature for 14 hours. The reaction solution was concentrated, and then partitioned between ethyl acetate and a saturated ammonium chloride aqueous solution. The organic layer was washed with a saturated sodium chloride solution, dried and concentrated, and the obtained residue was purified by a silica gel column (50 g, n-hexane:ethyl acetate=2:1) to obtain 433 mg (99%) of [2-(1H-indol-4-yloxy)ethyl]-methyl-carbamic acid tert-butyl ester as a viscous oily substance.

Workup

  1. concentrationThe reaction solution was concentrated
  2. custompartitioned between ethyl acetate
  3. washThe organic layer was washed with a saturated sodium chloride solution
  4. customdried
  5. concentrationconcentrated
  6. customthe obtained residue was purified by a silica gel column (50 g, n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-1611a08f6b4b4ed48e02a5eb4b76c68c
Source dataset
uspto-grants-2013_12
Patent number
US08609656B2

Reaction notes

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