Toluene → HCID 59453988, compound

HRID 1662057Notes

Reaction equation

HRID 1662057 reaction equation
[C:1]([C@@H:3]1[CH2:7][CH2:6][CH2:5][C@@H:4]1[NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])#[N:2].C1(C)C=CC=CC=1.[N-:23]=[N+:24]=[N-:25].[Na+].Cl.C(N(CC)CC)C>O>[N:2]1[NH:23][N:24]=[N:25][C:1]=1[C@@H:3]1[CH2:7][CH2:6][CH2:5][C@@H:4]1[NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 1140TolueneHCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 59454078HCID 59454078, compound

Product 1

HCID 59453988HCID 59453988, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of tert-butyl [(1S,2R)-2-cyanocyclopentyl]carbamate (2.8 g), toluene (50 ml), sodium azide (2.1 g), and triethylamine hydrochloride (4.5 g) was stirred at 130° C. for 24 hours. To the reaction mixture was added water (40 ml) at room temperature. The aqueous layer was separated, citric acid was added thereto under ice-cooling, and the solid precipitated was collected by filtration and washed with water to obtain tert-butyl [(1S,2R)-2-(2H-tetrazole-5-yl)cyclopentyl]carbamate (3.0 g).

Workup

  1. customThe aqueous layer was separated
  2. additioncitric acid was added
  3. temperatureunder ice-cooling
  4. customthe solid precipitated
  5. filtrationwas collected by filtration
  6. washwashed with water

Sources & evidence

ORD record
ord-33b2e05356d64a38b8cd6d7e18b73d0b
Source dataset
uspto-grants-2011_10
Patent number
US08030489B2

Reaction notes

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