Tetrabutylammonium Fluoride → HCID 89519959, compound

HRID 571653Notes

Reaction equation

HRID 571653 reaction equation
[Si]([O:18][CH2:19][C@@H:20]1[S:25][CH2:24][C@@H:23]([CH3:26])[NH:22][CH2:21]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH3:26][C@H:23]1[NH:22][CH2:21][C@H:20]([CH2:19][OH:18])[S:25][CH2:24]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 90407016HCID 90407016, compound

Product 1

HCID 89519959HCID 89519959, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2R,5R)-2-({[tert-butyl(diphenyl)silyl]oxy}methyl)-5-methylthiomorpholine (1, 0.200 g, 0.519 mmol) in THF (1 mL) was added tetrabutylammonium fluoride (1.0 M in THF, 0.778 mL, 0.778 mmol). The reaction was stirred at ambient temperature for 2 h, then concentrated in vacuo to provide crude [(2R,5R)-5-methylthiomorpholin-2-yl]methanol (2) that gave a mass ion (ES+) of 148.3 for M+H+.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cc2cb43b20e248f1865a6e9a79028ce5
Source dataset
uspto-grants-2015_05
Patent number
US09029364B2

Reaction notes

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