Sodium Azide → HCID 89510172, compound

HRID 245066Notes

Reaction equation

[C:1]([Si:5]([O:18][C@@H:19]1[C@@:24]2([CH3:25])[C@H:22]([O:23]2)[CH2:21][CH2:20]1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2].Cl([O-])(=O)(=O)=O.[Li+].[N-:32]=[N+:33]=[N-:34].[Na+]>>[N:32]([C@@H:22]1[CH2:21][CH2:20][C@@H:19]([O:18][Si:5]([C:1]([CH3:2])([CH3:4])[CH3:3])([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C@@:24]1([CH3:25])[OH:23])=[N+:33]=[N-:34]

Participants

Reactant 3

HCID 33557Sodium Azide

HCID 23665649Lithium perchlorate

HCID 89510183HCID 89510183, compound

Product 1

HCID 89510172HCID 89510172, compound

Conditions

Temperature: 90 °C

Procedure

The title compound is prepared by essentially following the procedure as described in Preparation 41 using rel-tert-butyl-[[(1R,4S,5R)-5-methyl-6-oxabicyclo[3.1.0]hexan-4-yl]oxy]-diphenyl-silane (enantiomeric mixture), except that the reaction is heated to 90° C. for 48 h and the addition of lithium perchlorate and the second addition of sodium azide are omitted.

Sources & evidence

ORD record: ord-f0dfeb3cdf7348c7bb96aaa8a6e4db54
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658693B2

Reaction notes

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