1,2-Dichloroethane → 3-Phenylpyrrolidine--hydrogen chloride (1/1)

HRID 657719Notes

Reaction equation

HRID 657719 reaction equation
CC(C)(C)CC([N:6]1[CH2:10][C@H:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C@@H:8](C=O)[CH2:7]1)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:35]CCCl>C(Cl)Cl>[ClH:35].[C:11]1([CH:9]2[CH2:10][NH:6][CH2:7][CH2:8]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 111,2-Dichloroethane2×HCID 5049666Sodium triacetoxyborohydrideHCID 86627743HCID 86627743, compound

Product 1

HCID 441188043-Phenylpyrrolidine--hydrogen chloride (1/1)Yield 8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 89 mg (0.35 mmol) of 1-isopropyl-3-methyl-bicyclo[3.2.1]-1β,3,8-triaza-spiro[4.5]dodecan-2,4-dione in DCE (5 mL) was added 97 mg (0.35 mmol) of (3R,4S)-1-(3,3-dimethyl-butyryl)-4-phenyl-pyrrolidine-3-carbaldehyde in DCE (5 mL) and stirred for 2 hours at room temperature. Sodium triacetoxyborohydride (113 mg, 0.53 mmol) was then added and the reaction mixture stirred overnight at room temperature. The reaction mixture was diluted with DCM, the organic layer washed with sodium bicarbonate, and then dried over sodium sulfate. The reaction mixture was filtered, purified by semi-preparative HPLC (Method B) and lyophilized to give (3S,4S)-1-(3,3-dimethyl-butyryl)-3-[1-isopropyl-3-methyl-bicyclo[3.2.1]-2,4-dioxo-1β,3,8-triaza-spiro[4.5]dodec-8-ylmethyl]-4-phenyl-pyrrolidine hydrochloride (16 mg, 8%).

Workup

  1. stirringthe reaction mixture stirred overnight at room temperature
  2. washthe organic layer washed with sodium bicarbonate
  3. dry with materialdried over sodium sulfate
  4. filtrationThe reaction mixture was filtered
  5. custompurified by semi-preparative HPLC (Method B)

Sources & evidence

ORD record
ord-4e2b18ad12ff445a8283c291c0fa45a8
Source dataset
uspto-grants-2011_12
Patent number
US08076349B2

Reaction notes

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