Benzyl Bromide → 5(S)-((t-butyl-dimethylsilyloxy)methyl)-3(R)-phenylmethyl-N-BOC-2-pyrrolidinone

HRID 36338Notes

Reaction equation

HRID 36338 reaction equation
[C:1]([Si:5]([CH3:22])([CH3:21])[O:6][CH2:7][C@H:8]1[N:12]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:11](=[O:20])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[CH2:33](Br)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C1COCC1>[C:1]([Si:5]([CH3:22])([CH3:21])[O:6][CH2:7][C@H:8]1[N:12]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:11](=[O:20])[C@H:10]([CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:9]1)([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 2733832Lithium HexamethyldisilazideHCID 109036131,1-Dimethylethyl (2S)-2-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-5-oxo-1-pyrrolidinecarboxylate

Product 1

HCID 146061105(S)-((t-butyl-dimethylsilyloxy)methyl)-3(R)-phenylmethyl-N-BOC-2-pyrrolidinone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5(S)-((t-butyl-dimethyl-silyloxy)methyl)-N-BOC-2-pyrrolidinone (400 mg, 1.26 mmol) in 2 ml of THF was added to a precooled (-78° C.) 1M solution of lithium hexamethyldisilazide (1.3 ml) in 5 ml of THF. After 45 min, 0.15 ml of benzyl bromide (1.3 mmol) was added and the stirring was continued. After 5 h the reaction was worked up by pouring into a separatory funnel containing 30 ml of an aqueous 10% citric solution. The aqueous layer was extracted (2×30 ml EtOAc) which was backwashed with brine (50 ml) dried, filtered and concentrated to an oil. The residue was chromatographed (SiO2, 20% EtOAc/Hexane) to afford the product as an oil.

Workup

  1. waitAfter 5 h the reaction was worked up
  2. additionby pouring into a separatory funnel
  3. extractionThe aqueous layer was extracted (2×30 ml EtOAc) which
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated to an oil
  7. customThe residue was chromatographed (SiO2, 20% EtOAc/Hexane)

Sources & evidence

ORD record
ord-cf76cd28958e492f9ffff0cf523c5594
Source dataset
uspto-grants-1995_05
Patent number
US05413999

Reaction notes

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