Tetrahydrofuran → (S)-4-(t-Butyldimethylsilyloxy)pyrrolidin-2-one

HRID 1632096Notes

Reaction equation

HRID 1632096 reaction equation
[C:1]([Si:5]([CH3:32])([CH3:31])[O:6][C@@H:7]1[CH2:11][N:10](CC2C=C(C3C=CC=C([N+]([O-])=O)C=3)C(OC)=CC=2)[C:9](=[O:30])[CH2:8]1)([CH3:4])([CH3:3])[CH3:2].C1COCC1.[H-].[Na+]>O>[C:1]([Si:5]([CH3:32])([CH3:31])[O:6][C@@H:7]1[CH2:11][NH:10][C:9](=[O:30])[CH2:8]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 58019967(S)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(6-methoxy-3'-nitro-biphenyl-3-ylmethyl)-pyrrolidin-2-one

Product 1

HCID 11074789(S)-4-(t-Butyldimethylsilyloxy)pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Synthesis of ((S)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(6-methoxy-3′-nitro-biphenyl-3-ylmethyl)-pyrrolidin-2-one (I-213). Into a 250 mL round-bottomed flask with a stir bar was added I-212 (2.57 g, 11.95 mmol), THF (150 mL), and the solution was cooled to 0° C. NaH (0.56 g, 14.12 mmol) was added and the suspension was stirred at room temperature for 30 minutes. To this, I-70 (3.50 g, 10.86 mmol) was added and the reaction was stirred for 20 hours at room temperature after which time 50 mL of water was added and the product was extracted with ethyl acetate. The organics were concentrated to yield 8.9 g of I-213, which was used as is in the next reaction.

Workup

  1. additionInto a 250 mL round-bottomed flask with a stir bar was added
  2. additionTo this, I-70 (3.50 g, 10.86 mmol) was added
  3. additionwas added
  4. extractionthe product was extracted with ethyl acetate
  5. concentrationThe organics were concentrated
  6. customto yield 8.9 g of I-213, which
  7. customas is in the next reaction

Sources & evidence

ORD record
ord-c1d75640d30b47caaa676d0b7f2aad6b
Source dataset
uspto-grants-2014_07
Patent number
US08791267B2

Reaction notes

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