Tetrabutylammonium Fluoride → Tert-butyl 2-(2-hydroxyethyl)-2-phenylmorpholine-4-carboxylate

HRID 271999Notes

Reaction equation

HRID 271999 reaction equation
[Si]([O:8][CH2:9][CH2:10][C:11]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[O:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.C(Cl)(Cl)Cl>[OH:8][CH2:9][CH2:10][C:11]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[O:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:21])[CH3:22])=[O:18])[CH2:12]1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59835991Tert-butyl 2-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-2-phenylmorpholine-4-carboxylate

Product 1

HCID 59835989Tert-butyl 2-(2-hydroxyethyl)-2-phenylmorpholine-4-carboxylateYield 83%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

The above tert-butyl 2-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-2-phenylmorpholine-4-carboxylate was stirred in 4 mL of a 1 M solution of tetrabutylammonium fluoride in THF for 1 h at room temperature. The reaction mixture was then diluted with CHCl3, washed with saturated aqueous NaHCO3, and purified (1:1 hex:EtOAc) to provide tert-butyl 2-(2-hydroxyethyl)-2-phenylmorpholine-4-carboxylate (449 mg, 83%) as an oil: 1H NMR (400 MHz, CDCl3), δ 7.47-7.41 (m, 2H), 7.40-7.35 (m, 2H), 7.28 (m, 1H), 4.34 (m, 1H), 3.77-3.63 (m, 2H), 3.63-3.48 (m, 3H), 3.35 (m, 1H), 3.17 (m, 1H), 2.08 (m, 1H), 1.89 (m, 1H), 1.50-1.37 (br., 9H); ESI-MS 330 (M+Na).

Workup

  1. washwashed with saturated aqueous NaHCO3
  2. custompurified (1:1 hex:EtOAc)

Sources & evidence

ORD record
ord-5c6455ebae7e4fc99d6594c9cc1476d8
Source dataset
uspto-grants-2008_11
Patent number
US07452992B2

Reaction notes

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