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

HRID 36339Notes

Reaction equation

HRID 36339 reaction equation
[Si]([O:8][CH2:9][C@H:10]1[N:14](C(OC(C)(C)C)=O)[C:13](=[O:22])[C@H:12]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:11]1)(C(C)(C)C)(C)C>C(#N)C.O>[OH:8][CH2:9][C@H:10]1[NH:14][C:13](=[O:22])[C@H:12]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:11]1

Participants

4

Reactant 1

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

Product 1

HCID 15152345(S)-hydroxymethyl-3(R)-phenylmethyl-2-pyrrolidinone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To 130 mg (0.34 mmol) of 5(S)-((t-butyl-dimethylsilyloxy)methyl)-3(R)-phenylmethyl-N-BOC-2-pyrrolidinone in 5 ml of acetonitrile was added 0.1 ml of a solution of 48% HF in water. After 3 hr at room temperature the reaction was concentrated to dryness and diluted with 30 ml of an aqueous 10% NaHCO3 solution. This was extracted with EtOAc (2×30 ml), dried filtered and concentrated to afford the crude product.

Workup

  1. concentrationAfter 3 hr at room temperature the reaction was concentrated to dryness
  2. additiondiluted with 30 ml of an aqueous 10% NaHCO3 solution
  3. extractionThis was extracted with EtOAc (2×30 ml)
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e568117ed25d494a80543a38f9100e98
Source dataset
uspto-grants-1995_05
Patent number
US05413999

Reaction notes

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