Tetrahydrofuran → HCID 178436524, compound

HRID 1639992Notes

Reaction equation

HRID 1639992 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-5074fd739f3a40539a5fbbfdf708f80d
Source dataset
uspto-grants-2012_02
Patent number
US08110581B2

Reaction notes

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