Phosphoric Acid → (S)-2-(((tert-Butyldiphenylsilyl)oxy)methyl)-5-(pyrrolidin-2-yl)-1,3,4-oxadiazole

HRID 710044Notes

Reaction equation

HRID 710044 reaction equation
[Si:1]([O:18][CH2:19][C:20]1[O:24][C:23]([C@@H:25]2[CH2:29][CH2:28][CH2:27][N:26]2C(OC(C)(C)C)=O)=[N:22][N:21]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OP(O)(O)=O.[OH-].[Na+]>C1COCC1>[Si:1]([O:18][CH2:19][C:20]1[O:24][C:23]([C@@H:25]2[CH2:29][CH2:28][CH2:27][NH:26]2)=[N:22][N:21]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 1004Phosphoric AcidHCID 14798Sodium HydroxideHCID 86706755(S)-t-Butyl 2-(5-(((tert-butyldiphenylsilyl)oxy)methyl)-1,3,4-oxadiazol-2-yl)pyrrolidine-1-carboxylate

Product 1

HCID 86706756(S)-2-(((tert-Butyldiphenylsilyl)oxy)methyl)-5-(pyrrolidin-2-yl)-1,3,4-oxadiazoleYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a THF (3.8 mL) solution of the compound (3.832 g) obtained in Example 9-(2), H3PO4 (6.1 mL, 85% aqueous solution) was added and the mixture was stirred at room temperature for an hour. To the reaction mixture, THF (50 mL) was added and the resulting mixture was added to NaOH (150 mL, 1.0 N aqueous solution) and ice (50 g), followed by extraction with CHCl3 (300 mL). The organic layer was dried (Na2SO4), filtered and concentrated to give a crude product, which was further purified by NH-form silica gel chromatography (MeOH/CHCl3) to give the titled compound (1.261 g, colorless oil.)

Workup

  1. extractionfollowed by extraction with CHCl3 (300 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a crude product, which
  6. customwas further purified by NH-form silica gel chromatography (MeOH/CHCl3)

Sources & evidence

ORD record
ord-a2ab0069223f4d08be851c0d8d5b82f9
Source dataset
uspto-grants-2015_11
Patent number
US09181229B2

Reaction notes

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