Ammonium Chloride → HCID 66967852, compound

HRID 598570Notes

Reaction equation

[CH3:1][Si:2]([CH3:17])([CH3:16])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8]1.C([Li])CCC.[C:23]([O:27][C:28]([N:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH:31]1[C:36](=[O:41])N(OC)C)=[O:29])([CH3:26])([CH3:25])[CH3:24].[NH4+].[Cl-]>COCCOC>[C:23]([O:27][C:28]([N:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH:31]1[C:36]([C:8]1[N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:17])([CH3:16])[CH3:1])[C:15]2[C:10]([CH:9]=1)=[CH:11][CH:12]=[CH:13][CH:14]=2)=[O:41])=[O:29])([CH3:26])([CH3:25])[CH3:24]

Participants

Conditions

Temperature: 2.5 °C

Procedure

A stirring, ice-cooled solution of 1-(2-trimethylsilanyl-ethoxymethyl)-1H-indole, D66 (742 mg, 3 mmol) in DME (5 ml) was treated drop-wise with n-butyl lithium (2.2 ml, 1.6M in hexanes, 3.5 mmol). The resulting green solution was stirred at 0-5° C. for 15 min. then was treated with (RS)-1-(tert-butyloxycarbonyl)-2-(N-methoxy-N-methylcarbamoyl)-piperidine, D1 (952 mg, 3.5 mmol) in DME (2.5 ml). After stirring at this temperature for a further 45 min. saturated aqueous NH4Cl was added (10 ml) and the product was extracted with diethyl ether. The organics were combined, the solvent removed in vacuo and the residue chromatographed (silica gel, 10% diethyl ether-pentane) to afford the title compound as a colourless oil (510 mg, 37%).

Workup

additionwas added (10 ml)
extractionthe product was extracted with diethyl ether
customthe solvent removed in vacuo
customthe residue chromatographed (silica gel, 10% diethyl ether-pentane)

Sources & evidence

ORD record: ord-eebb79d0d8f44ab8807d357129a66a1b
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897618B2

Reaction notes

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