Ammonia → (3S,4S)-3-(tert-Butoxycarbonyl)amino-4-vinylpyrrolidine

HRID 1253423Notes

Reaction equation

HRID 1253423 reaction equation
C(OC([N:11]1[CH2:15][C@H:14]([CH:16]=[CH2:17])[C@H:13]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:12]1)=O)C1C=CC=CC=1.[Na].N>O1CCCC1>[C:22]([O:21][C:19]([NH:18][C@H:13]1[C@@H:14]([CH:16]=[CH2:17])[CH2:15][NH:11][CH2:12]1)=[O:20])([CH3:25])([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 5360545SodiumHCID 59665269(3S,4S)-1-Benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-vinylpyrrolidine

Product 1

HCID 22880744(3S,4S)-3-(tert-Butoxycarbonyl)amino-4-vinylpyrrolidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (3S,4S)-1-benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-vinylpyrrolidine (275 mg, 0.794 mmol) in tetrahydrofuran (5 mL) and sodium (300 mg, 13.0 mmol) were sequentially added to liquid ammonia (80 mL) at −78° C., and the mixture was stirred at the same temperature for 0.5 hours. The solvent was removed, followed by dilution with chloroform (80 mL). The resultant mixture was washed sequentially by 1 mol/L sodium hydroxide (30 mL) and saturated brine (100 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure, to thereby yield the title compound as a colorless oily substance (168 mg, 100).

Workup

  1. customThe solvent was removed
  2. washThe resultant mixture was washed sequentially by 1 mol/L sodium hydroxide (30 mL) and saturated brine (100 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ef29971289824ba7880d8c761070b6d5
Source dataset
uspto-grants-2013_06
Patent number
US08455482B2

Reaction notes

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