(S)-3-tert-Butoxycarbonylamino-1-[4-({[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]ethylamino}methyl)piperidin-1-yl]-propan-1-one → (S)-3-amino-1-[4-({[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]ethylamino}-methyl)piperidin-1-yl]propan-1-one

HRID 429832Notes

Reaction equation

HRID 429832 reaction equation
C(OC([NH:8][CH2:9][CH2:10][C:11]([N:13]1[CH2:18][CH2:17][CH:16]([CH2:19][N:20]([C@@H:23]([CH3:34])[CH2:24][C:25]2[CH:26]=[CH:27][C:28]3[O:32][CH2:31][CH2:30][C:29]=3[CH:33]=2)[CH2:21][CH3:22])[CH2:15][CH2:14]1)=[O:12])=O)(C)(C)C>FC(F)(F)C(O)=O>[NH2:8][CH2:9][CH2:10][C:11]([N:13]1[CH2:18][CH2:17][CH:16]([CH2:19][N:20]([C@@H:23]([CH3:34])[CH2:24][C:25]2[CH:26]=[CH:27][C:28]3[O:32][CH2:31][CH2:30][C:29]=3[CH:33]=2)[CH2:21][CH3:22])[CH2:15][CH2:14]1)=[O:12]

Participants

3

Reactant 1

HCID 54233503(S)-3-tert-Butoxycarbonylamino-1-[4-({[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]ethylamino}methyl)piperidin-1-yl]-propan-1-one

Product 1

HCID 54502007(S)-3-amino-1-[4-({[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]ethylamino}-methyl)piperidin-1-yl]propan-1-oneYield 99%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To (S)-3-tert-Butoxycarbonylamino-1-[4-({[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]ethylamino}methyl)piperidin-1-yl]-propan-1-one (0.76 grams, 1.60 mmol) was added 20% trifluroacetic acid (20 ml). The reaction mixture was stirred at room temperature for 4 hours. The mixture was concentrated under reduced pressure and the residue was partitioned between dichloromethane and 1N sodium hydroxide. The organic layer was washed with water, dried over potassium carbonate and concentrated to give (S)-3-amino-1-[4-({[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]ethylamino}methyl)piperidin-1-yl]-propan-1-one as an oil (0.59 grams, 99%), M+H 373.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between dichloromethane and 1N sodium hydroxide
  3. washThe organic layer was washed with water
  4. dry with materialdried over potassium carbonate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6aa7e38f50d84cf79b4effff3d2c7caa
Source dataset
uspto-grants-2001_11
Patent number
US06319920B1

Reaction notes

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