Sodium triacetoxyborohydride → 1-Boc-3-Phenyl-pyrrolidine

HRID 657717Notes

Reaction equation

HRID 657717 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@@H:10](C=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 5049666Sodium triacetoxyborohydrideHCID 58981949(3R,4S)-3-formyl-4-phenyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 112303881-Boc-3-Phenyl-pyrrolidine

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To 527 mg (2.22 mmol) of 1-isopropyl-3-methyl-bicyclo[3.2.1]-1β,3,8-triaza-spiro[4.5]dodecan-2-one in DCE (15 mL) was added 611 mg (2.22 mmol) of (3R,4S)-3-formyl-4-phenyl-pyrrolidine-1-carboxylic acid tert-butyl ester in DCE (10 mL) and stirred for 2 hours at room temperature. Sodium triacetoxyborohydride (706 mg, 3.33 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 organic layer was concentrated and purified by flash silica gel chromatography eluting with methanol:DCM (0-10%) to give 612 mg (56%) of (3S,4S)-3-[1-isopropyl-3-methyl-bicyclo[3.2.1]-2-oxo-1β,3,8-triaza-spiro[4.5]dodec-8-ylmethyl]-4-phenyl-pyrrolidine-1-carboxylic acid tert-butyl ester as a white foam.

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. concentrationThe organic layer was concentrated
  5. custompurified by flash silica gel chromatography
  6. washeluting with methanol

Sources & evidence

ORD record
ord-bc7132f6b17c4d51a4e4d70f91e5d231
Source dataset
uspto-grants-2011_12
Patent number
US08076349B2

Reaction notes

Loading…