Dimethyl Sulfoxide → HCID 59835986, compound

HRID 272000Notes

Reaction equation

HRID 272000 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:9][CH2:8][CH2:7][N:6]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:5]1.CS(C)=O.C(N(C(C)C)CC)(C)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[O:1]=[CH:2][CH2:3][C:4]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:9][CH2:8][CH2:7][N:6]([C:10]([O:12][C:13]([CH3:16])([CH3:14])[CH3:15])=[O:11])[CH2:5]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 59835989Tert-butyl 2-(2-hydroxyethyl)-2-phenylmorpholine-4-carboxylate

Product 1

HCID 59835986HCID 59835986, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of tert-butyl 2-(2-hydroxyethyl)-2-phenylmorpholine-4-carboxylate (428 mg, 1.4 mmol), dimethyl sulfoxide (4.0 mL, 56.4 mmol) and diisopropylethylamine (1.3 mL, 7.2 mmol) in 8 mL CH2Cl2 was added SO3.pyr (1.4 g, 8.8 mmol) and the reaction mixture was stirred for 2 h. After the addition of saturated aqueous NaHCO3, the solution was extracted with CHCl3, and passed through a plug of silica gel flushing with 2:1 hex:EtOAc to provide tert-butyl 2-(2-oxoethyl)-2-phenylmorpholine-4-carboxylate (226 mg, 53%) as a clear oil. 1H NMR (400 MHz, CDCl3), δ 9.60 (br. s, 1H), 7.54-7.44 (br., 2H), 7.42-7.37 (m, 2H), 7.30 (m, 1H), 4.25-4.01 (br., 1H), 3.80-3.23 (m, 5H), 3.00-2.81 (m, 2H), 2.73 (br., 1H), 1.47 (br., 9H); ESI-MS 328 (M+H).

Workup

  1. extractionthe solution was extracted with CHCl3

Sources & evidence

ORD record
ord-3017e9b0cb1243cab0ff31ba97e93bbe
Source dataset
uspto-grants-2008_11
Patent number
US07452992B2

Reaction notes

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