Tetrahydrofuran → HCID 178436524, compound

Reaction equation

[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([N:8]2[CH2:12][CH2:11][C@:10]3([CH2:17][CH2:16][CH2:15][N:14]([C:18]4[C:23]([C:24]#[C:25][Si](C)(C)C)=[CH:22][CH:21]=[CH:20][N:19]=4)[CH2:13]3)[C:9]2=[O:30])[CH2:4][CH2:3]1.O.[OH-].[Li+].O1CCCC1>O>[C:24]([C:23]1[C:18]([N:14]2[CH2:15][CH2:16][CH2:17][C@@:10]3([C:9](=[O:30])[N:8]([C@H:5]4[CH2:6][CH2:7][C@H:2]([OH:1])[CH2:3][CH2:4]4)[CH2:12][CH2:11]3)[CH2:13]2)=[N:19][CH:20]=[CH:21][CH:22]=1)#[CH:25]

Participants

Procedure

A mixture of (5S)-2-(trans-4-hydroxycyclohexyl)-7-{3-[(trimethylsilyl)ethynyl]pyridin-2-yl}-2,7-diazaspiro[4.5]decan-1-one (10 mg, 0.00002 mol, this compound was prepared by using procedures analogous to those described for the synthesis of example 93), lithium hydroxide monohydrate (1.1 mg, 0.000026 mol) in tetrahydrofuran (0.5 mL, 0.006 mol) and a couple of drops of water was stirred at rt for 30 min. The crude reaction mixture was purified by prep-HPLC to afford 7.2 mg of the desired product. LC-MS: 354.2 (M+H)+.