Ammonium Chloride → (R)-5-(1-Boc-pyrrolidin-2-YL)-1H-tetrazole

HRID 2243880Notes

Reaction equation

HRID 2243880 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[C:13]#[N:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:15]=[N+:16]=[N-:17].[Na+].[Cl-].[NH4+]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[C:13]1[N:15]=[N:16][NH:17][N:14]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 2756788tert-butyl (2R)-2-cyanopyrrolidine-1-carboxylate

Product 1

HCID 24780601(R)-5-(1-Boc-pyrrolidin-2-YL)-1H-tetrazoleYield 52.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound of Example 11 (8.34 g, 42.5 mmol), sodium azide (3.04 g, 46.8 mmol), and ammonium chloride (2.50 g, 46.8 mmol) were stirred in DMF (30 mL) at 100° C. for 12 h. The reaction was concentrate and partitioned with DCM and 3 M HCl. The organic extracts were dried over sodium sulphate, filtered and concentrated. The resulting solid was triturated with ether and filtered to afford the title product (5.31 g, 52%) as a white solid.

Workup

  1. concentrationThe reaction was concentrate
  2. custompartitioned with DCM and 3 M HCl
  3. dry with materialThe organic extracts were dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting solid was triturated with ether
  7. filtrationfiltered

Sources & evidence

ORD record
ord-47630bc9f0904c589f04c7fd40f9e549
Source dataset
uspto-grants-2010_03
Patent number
US07678796B2

Reaction notes

Loading…