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

HRID 730576Notes

Reaction equation

HRID 730576 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[C:11]([O:15][C:16](=[O:22])[N:17]([CH2:19][CH2:20]O)[CH3:18])([CH3:14])([CH3:13])[CH3:12].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[C:11]([O:15][C:16](=[O:22])[N:17]([CH2:19][CH2:20][O:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2)[CH3:18])([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 754211H-indol-4-olHCID 545700N-(tert-Butoxycarbonyl)-N-methyl-2-aminoethanolHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 10708626[2-(1H-indol-4-yloxy)ethyl]-methylcarbamic acid tert-butyl esterYield 70.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (0° C.) solution of 4-hydroxyindole (2.92 g) and (2-hydroxy-ethyl)-methyl-carbamic acid tert-butyl ester (3.50 g) in 100 mL of THF was added PPh3 (5.8 g) followed by the dropwise addition of diisopropylazodicarboxylate (4.44 g) over 10 minutes. After 16 h the reaction was worked up in the normal manner and the crude oil was purified by chromatography to afford 4.1 g of [2-(1H-indol-4-yloxy)-ethyl]-methyl-carbamic acid tert-butyl ester. MS: 313 (M+Na)+.

Workup

  1. customthe crude oil was purified by chromatography

Sources & evidence

ORD record
ord-654acd45167344d5af65693edff7b0a4
Source dataset
uspto-grants-2009_09
Patent number
US07582760B2

Reaction notes

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