Ammonium Chloride → (2S,4R,5R)-5-Azido-2-benzhydryl-tetrahydro-pyran-4-ol

HRID 78939Notes

Reaction equation

HRID 78939 reaction equation
[CH:1]([C@@H:14]1[CH2:20][C@@H:19]2[C@@H:17]([O:18]2)[CH2:16][O:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.O.[N-:24]=[N+:25]=[N-:26].[Na+].[NH4+].[Cl-]>CCOCC>[N:24]([C@@H:17]1[CH2:16][O:15][C@H:14]([CH:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:20][C@H:19]1[OH:18])=[N+:25]=[N-:26]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 22242641Methanol--water (1/1)HCID 54762329(1S,4S,6R)-4-benzhydryl-3,7-dioxa-bicyclo[4.1.0]-heptane

Product 1

HCID 11716531(2S,4R,5R)-5-Azido-2-benzhydryl-tetrahydro-pyran-4-olYield 95%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
80 °C

Procedure

A solution of (1S,4S,6R)-4-benzhydryl-3,7-dioxa-bicyclo[4.1.0]-heptane 28a (0.05 g, 0.19 mmol) in a 8:1 MeOH/H2O (2 ml) mixture was treated with NaN3 (0.061 g, 0.94 mmol) and NH4Cl (0.022 g, 0.41 mmol) and the resulting reaction mixture was stirred at 80° C. overnight. The reaction mixture was diluted with ether and the organic layer was separated. Evaporation of the washed (saturated aqueous NaHCO3, water) ether extracts afforded a crude solid product. Purification of the product by flash chromatography (Hexane/Ethyl Acetate=4:1) yielded (2S,4R,5R)-5-Azido-2-benzhydryl-tetrahydropyran-4-ol 30a 0.05 g (95%, [α]D=(−)109.3, c=1, MeOH).

Workup

  1. customthe resulting reaction mixture
  2. customthe organic layer was separated
  3. customEvaporation of the
  4. washwashed (saturated aqueous NaHCO3, water) ether
  5. customextracts afforded a crude solid product
  6. customPurification of the product by flash chromatography (Hexane/Ethyl Acetate=4:1)

Sources & evidence

ORD record
ord-752a719f3aa24c2395fab644f0ebe136
Source dataset
uspto-grants-2014_09
Patent number
US08841464B2

Reaction notes

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