Sodium Azide → HCID 16732282, compound

HRID 501652Notes

Reaction equation

HRID 501652 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[C@H:9]1[C@@H:21](OS(C)(=O)=O)[CH3:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:28]=[N+:29]=[N-:30].[Na+]>CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[C@H:9]1[C@H:21]([N:28]=[N+:29]=[N-:30])[CH3:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 59424835(2S,3S)-N-tert-Butyloxycarbonyl-3-(tert-butyldimethylsilanyloxy)-2-((1S)-1-methanesulfonyloxyethyl)pyrrolidine

Product 1

HCID 16732282HCID 16732282, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 80B (650 mg, 1.53 mmol) and sodium azide (597 mg, 9.18 mmol) was heated at 80° C. for 2 days. The reaction was diluted with EtOAc (200 mL), washed with brine:water (1:1, 4×15 mL), dried (MgSO4), filtered and concentrated to give the crude product. Purification by chromatography (40 g ISCO silica gel cartridge, 0-20% EtOAc/hexane) provided 80C as a colorless oil (410 mg). MS (ES) m/z 271 [M-Boc+H]+.

Workup

  1. washwashed with brine:water (1:1, 4×15 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give the crude product
  6. customPurification by chromatography (40 g ISCO silica gel cartridge, 0-20% EtOAc/hexane)

Sources & evidence

ORD record
ord-c9664006f3fb40c591339eeb71c855d6
Source dataset
uspto-grants-2010_08
Patent number
US07772267B2

Reaction notes

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