Water → HCID 86603712, compound

HRID 2376091Notes

Reaction equation

HRID 2376091 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[CH2:5][N:6]1[CH2:10][CH2:9][C@@H:8]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:7]1.N1C=CC=CC=1.[C:28](OC(=O)C)(=[O:30])[CH3:29].O>C(Cl)Cl>[C:28]([NH:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[CH2:5][N:6]1[CH2:10][CH2:9][C@@H:8]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:7]1)(=[O:30])[CH3:29]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 86603711HCID 86603711, compound

Product 1

HCID 86603712HCID 86603712, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl [(3R)-1-(3-aminobenzyl)-3-pyrrolidinyl]carbamate (681 mg) in CH2Cl2 (6.8 mL) was added pyridine (28:4 uL), acetic anhydride (265 uL), and N,N-dimethylaminopyridine (14 mg), which was stirred at room temperature for 1.5 hours. To the resultant was added H2O. The mixture was extracted with CH2Cl2. The organic phase was washed by brine, dried over Na2SO4, filtered, and evaporated in vacuo to give tert-butyl {(3R)-1-[3-(acetylamino)benzyl]-3-pyrrolidinyl}carbamate (944 mg) as a off-white amorphous.

Workup

  1. extractionThe mixture was extracted with CH2Cl2
  2. washThe organic phase was washed by brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-baf9d9509b3b48beb7bc23ce09dc5aa2
Source dataset
uspto-grants-2008_12
Patent number
US07465731B2

Reaction notes

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