Tetrahydrofuran → HCID 178436524, compound

HRID 1044377Notes

Reaction equation

HRID 1044377 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

5

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 178504181HCID 178504181, compound

Product 1

HCID 178436524HCID 178436524, compound

Reagents, catalysts & solvents 1

HCID 962WaterCatalyst

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)+.

Workup

  1. customthis compound was prepared
  2. customThe crude reaction mixture
  3. customwas purified by prep-HPLC

Sources & evidence

ORD record
ord-80b394925562420587e2f86d8774a585
Source dataset
uspto-grants-2013_10
Patent number
US08563570B2

Reaction notes

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