Sodium Hydroxide → HCID 69083750, compound

HRID 594393Notes

Reaction equation

HRID 594393 reaction equation
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[F:11][C:12]([F:30])([F:29])[O:13][C:14]1[CH:28]=[CH:27][C:17]([CH2:18][N:19]2[C:24](=[O:25])[CH2:23][CH2:22][CH2:21][C:20]2=[O:26])=[CH:16][CH:15]=1.[P:31](Cl)(=[O:46])([O:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[O:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.[OH-].[Na+]>C1COCC1>[P:31]([O:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)([O:39][C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)([O:26][C:20]1[N:19]([CH2:18][C:17]2[CH:16]=[CH:15][C:14]([O:13][C:12]([F:29])([F:11])[F:30])=[CH:28][CH:27]=2)[C:24](=[O:25])[CH2:23][CH2:22][CH:21]=1)=[O:46]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 75654Diphenyl chlorophosphateHCID 2733832Lithium HexamethyldisilazideHCID 69083181HCID 69083181, compound

Product 1

HCID 69083750HCID 69083750, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent4×

Procedure

A cooled (0° C.) solution of 1 M LHMDS in THF (1.25 ml; 1.25 mmol; 1.2 equiv.) in anh. THF (2 ml) was treated dropwise with a solution of 1-(4-(trifluoromethoxy)benzyl)piperidine-2,6-dione (300 mg; 1.04 mmol; 1.0 equiv.) in anh. THF (2 ml), and the resulting mixture was stirred at rt, under nitrogen, for 1 h. The obtained mixture was cooled to −78° C., and treated with a solution of diphenyl phosphorochloridate (343 mg; 1.25 mmol; 1.2 equiv.) in anh. THF (1 ml). Stirring was continued at −78° C. for 10 min., and at rt for 1.5 h. A solution of 10% aq. NaOH (25 ml) was added, and the obtained mixture was extracted with Et2O (3×). The mixed organic layers were dried over anh. K2CO3, filtered, and concentrated to dryness under reduced pressure affording 6-oxo-1-(4-(trifluoromethoxy)benzyl)-1,4,5,6-tetrahydropyridin-2-yl diphenyl phosphate as a yellow oil which was directly used for the next reaction. LC-MS (conditions E): tR=0.84 min.; [M+H]+: 520.19 g/mol.

Workup

  1. temperatureThe obtained mixture was cooled to −78° C.
  2. stirringStirring
  3. waitwas continued at −78° C. for 10 min.
  4. waitat rt for 1.5 h
  5. extractionthe obtained mixture was extracted with Et2O (3×)
  6. dry with materialThe mixed organic layers were dried over anh. K2CO3
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-62229a1c317e4afc947323e23f530229
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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