5-(5-Hydroxy-pent-1-ynyl)-indole-1-carboxylic acid tert-butyl ester → 5-(5-Hydroxy-pentyl)-indole-1-carboxylic acid tert-butyl ester

HRID 1633644Notes

Reaction equation

HRID 1633644 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]#[C:18][CH2:19][CH2:20][CH2:21][OH:22])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][OH:22])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 695483925-(5-Hydroxy-pent-1-ynyl)-indole-1-carboxylic acid tert-butyl ester

Product 1

HCID 695524055-(5-Hydroxy-pentyl)-indole-1-carboxylic acid tert-butyl esterYield 97.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2.85 g (9.5 mmol) 5-(5-Hydroxy-pent-1-ynyl)-indole-1-carboxylic acid tert-butyl ester in 100 ml MeOH were subjected to hydrogenation with 300 mg 10%Pd/C to yield 2.8 g 5-(5-Hydroxy-pentyl)-indole-1-carboxylic acid tert-butyl ester as colorless oil, MS: 303 (M). To the crude material in 60 ml CH2Cl2, 0.87 ml (11 mmol) methanesulfonyl chloride and 3.8 ml (27 mmol) triethyl amine were added at 0° C. The solution was stirred at RT for 1 h.

Sources & evidence

ORD record
ord-d9eb208d4a6b462c95e64bc7e39501f7
Source dataset
uspto-grants-2003_01
Patent number
US06503907B2

Reaction notes

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