Toluene → (3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidine

HRID 1941533Notes

Reaction equation

HRID 1941533 reaction equation
C[Si](C)(C)CCO.CC(OCC1CS[C@@H]2[C@H:17](N)[C:18](=O)[N:15]2[C:14]=1[C:23](O)=O)=O.[Cl-].[NH4+:27].CC[O:30][C:31](C)=[O:32].[C:34]1([CH3:40])[CH:39]=CC=C[CH:35]=1>CN(C)C1C=CN=CC=1>[C:34]([O:32][C:31]([NH:27][C@H:17]1[CH2:23][CH2:14][NH:15][CH2:18]1)=[O:30])([CH3:40])([CH3:39])[CH3:35]

Participants

7

Reactant 5

HCID 1140TolueneHCID 8857Ethyl AcetateHCID 180132-(Trimethylsilyl)ethanolHCID 25517Ammonium ChlorideHCID 4413287-Aminocephalosporanic acid

Product 1

HCID 1514396(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidine

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

To a solution of 2-(trimethylsilyl)ethanol (33 mL) in toluene (80 mL) is added 4-dimethylaminopyridine (0.82 g), under N2. Compound 1 (11.4 g) (prepared in the same manner as Compound 3 in Example 24) is added and the mixture is heated to reflux. Upon completion, the reaction mixture is cooled and saturated ammonium chloride (125 mL) is added, followed by the addition of EtOAc (150 mL). The layers are separated and the EtOAc portion is washed with water (4×50 mL) and brine (2×40 mL), and dried (MgSO4). The solvents are removed in vacuo and the residue is subjected to column chromatography (silica) to provide Compound 2.

Workup

  1. additionis added
  2. temperaturethe mixture is heated to reflux
  3. temperatureUpon completion, the reaction mixture is cooled
  4. customThe layers are separated
  5. washthe EtOAc portion is washed with water (4×50 mL) and brine (2×40 mL)
  6. dry with materialdried (MgSO4)
  7. customThe solvents are removed in vacuo

Sources & evidence

ORD record
ord-bda75a70d5df45ce8697e24844abccef
Source dataset
uspto-grants-1997_12
Patent number
US05703231

Reaction notes

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