Water → HCID 53788886, compound

HRID 1700778Notes

Reaction equation

HRID 1700778 reaction equation
[Si]([O:18][CH2:19][C@@H:20]([N:22]1[CH2:26][CH2:25][CH2:24][C:23]1=[O:27])[CH3:21])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[O:27]=[C:23]1[CH2:24][CH2:25][CH2:26][N:22]1[C@@H:20]([CH3:21])[CH2:19][OH:18]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 69946440HCID 69946440, compound

Product 1

HCID 53788886HCID 53788886, compoundYield 199.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 0° C. solution of 11.20 g (29.4 mmol) of (S)-2-(2-oxopyrrolidin-1-yl)propyl tert-butyldiphenylsilyl ether (Part B) in 100 mL of THF was treated with 36.0 mL (36 mmol) of tetrabutylammonium fluoride (1 M in THF). The reaction was stirred at ambient temperature until tic analysis indicated the complete disappearance of starting material (30 min). The reaction was poured into 300 mL of H2O and the mixture extracted with CH2Cl2 (3×300 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo to give 8.40 g of the corresponding (S)-2-(2-oxopyrrolidin-1-yl)propyl alcohol which was used without purification.

Workup

  1. customthe complete disappearance of starting material (30 min)
  2. extractionthe mixture extracted with CH2Cl2 (3×300 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f6295563120a47a5a9ae0595990d6750
Source dataset
uspto-grants-2002_02
Patent number
US06350774B1

Reaction notes

Loading…