Tetrabutylammonium Fluoride → HCID 59437163, compound

HRID 75161Notes

Reaction equation

HRID 75161 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Si]([O:36][CH2:37][C@@H:38]1[CH2:42][N:41]([CH2:43][C:44]23[CH2:53][CH:48]4[CH2:49][CH:50]([CH2:52][CH:46]([CH2:47]4)[CH2:45]2)[CH2:51]3)[C:40](=[O:54])[NH:39]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1>C1COCC1>[C:44]12([CH2:43][N:41]3[CH2:42][C@@H:38]([CH2:37][OH:36])[NH:39][C:40]3=[O:54])[CH2:45][CH:46]3[CH2:47][CH:48]([CH2:49][CH:50]([CH2:52]3)[CH2:51]1)[CH2:53]2

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68477189(S)-4-((tert-butyldiphenylsilyloxy)methyl)-1-(1-adamantylmethyl)imidazolidin-2-one

Product 1

HCID 59437163HCID 59437163, compoundYield 32.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBAF (400 mg, 1.6 mmol) was added to a solution of (S)-4-((tert-butyldiphenylsilyloxy)methyl)-1-(1-adamantylmethyl)imidazolidin-2-one (261 mg, 0.52 mmol) in anhydrous THF (5 mL) at 0° C. The reaction was stirred at rt overnight. The reaction solution was concentrated to give the residue, which was purified by preparative TLC (PE/EtOAc 1/1) to provide (S)-1-(1-adamantylmethyl)-4-(hydroxymethyl)imidazolidin-2-one (45 mg, 10%). 1H NMR: (CDCl3, 400 MHz): δ=1.54 (s, 6H), 1.62-1.73 (m, 6H), 1.98 (s, 3H), 2.77 (m, 2H), 3.35 (m, 1H), 3.55-3.75 (m, 3H), 3.82 (m, 1H); MS m/z=265

Workup

  1. concentrationThe reaction solution was concentrated
  2. customto give the residue, which
  3. customwas purified by preparative TLC (PE/EtOAc 1/1)

Sources & evidence

ORD record
ord-e48951fdcfe04bfa902cb85065c02573
Source dataset
uspto-grants-2014_09
Patent number
US08835426B2

Reaction notes

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