[1-(S)-(1-Benzyl-pyrrolidin-3-(R)-ylcarbamoyl)-2,2-dimethyl-propyl]-carbamic acid tert-butyl ester → 2-(S)-Amino-N-(1-benzyl-pyrrolidin-3-(R)-yl)-3,3-dimethyl-butyramide

HRID 268608Notes

Reaction equation

HRID 268608 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:13](=[O:27])[NH:14][C@@H:15]1[CH2:19][CH2:18][N:17]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:16]1)[C:9]([CH3:12])([CH3:11])[CH3:10])(C)(C)C>FC(F)(F)C(O)=O.ClCCl>[NH2:7][C@@H:8]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:13]([NH:14][C@@H:15]1[CH2:19][CH2:18][N:17]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:16]1)=[O:27]

Participants

3

Reactant 1

HCID 58715018[1-(S)-(1-Benzyl-pyrrolidin-3-(R)-ylcarbamoyl)-2,2-dimethyl-propyl]-carbamic acid tert-butyl ester

Product 1

HCID 210623362-(S)-Amino-N-(1-benzyl-pyrrolidin-3-(R)-yl)-3,3-dimethyl-butyramide

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of 1a (0.80 g, 2.06 mmole) in 40% trifluoroacetic acid/dichloromethane (15 mL) was stirred at room temperature for 4 h. The solvent was removed by rotary evaporation, and the resulting organic residue was carefully partitioned between dichloromethane and a saturated solution of sodium bicarbonate (30 mL each). The organic extract was dried over anhydrous sodium sufate, filtered, and concentrated to give 2a as a light brown oil. This amine was used without further purification.

Workup

  1. customThe solvent was removed by rotary evaporation
  2. customthe resulting organic residue was carefully partitioned between dichloromethane
  3. extractionThe organic extract
  4. dry with materialwas dried over anhydrous sodium sufate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6bb288b443014d99a024b0c3c304e320
Source dataset
uspto-grants-2008_11
Patent number
US07446115B2

Reaction notes

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