Ammonium Chloride → methyl 2-hydroxy-2-(1-methyl-1H-indol-3-yl)acetate

HRID 1288651Notes

Reaction equation

[Li+].CC([N-]C(C)C)C.[CH3:9][N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:11]1.CC1(C)[C@@]23[C@@]4(ON4S(=O)(=[O:32])C2)C[C@H]1CC3.[Cl-].[NH4+]>O1CCCC1>[OH:32][CH:19]([C:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:10]([CH3:9])[CH:11]=1)[C:20]([O:22][CH3:23])=[O:21]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 2.87 millimole of LDA in 5 mL of dry tetrahydrofuran at -78° C. was added dropwise a solution of 0.53 g of methyl 2-(1-methyl-3-indolyl)acetate in 5 mL of dry tetrahyrofruan. The mixture was stirred for 30 minutes at -78° C., and then 0.9 g of (+)-(2R,8aS)-(camphorsulfonyl)oxaziridine was added. The mixture was warmed to room temperature and stirred for 2 hours. Then the mixture was poured into a solution of saturated aqueous ammonium chloride, and then extracted with diethyl ether. The ether extract was dried with magnesium sulfate and concentrated by evaporation. The residue was subjected to silica gel chromatography using a developing solution of dichloromethane/ethyl acetate (98:2 by volume) to give 0.38 g of an oily product.

Workup

temperatureThe mixture was warmed to room temperature
stirringstirred for 2 hours
extractionextracted with diethyl ether
extractionThe ether extract
dry with materialwas dried with magnesium sulfate
concentrationconcentrated by evaporation

Sources & evidence

ORD record: ord-bc29dd460ed14424aadf395cd905b66a
Source dataset: uspto-grants-1998_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05747236

Reaction notes

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