(R)-2-Azido-1-[4-(benzyloxy)-3-[[(tert-butyldimethylsilyl)oxy]methyl]phenyl]ethanol → (R)-4-(2-Amino-1-hydroxyethyl)-2-[[(tert-butyldimethylsilyl)oxy]methyl]phenol

HRID 385247Notes

Reaction equation

HRID 385247 reaction equation
NC[C@@H](C1C=CC(O)=C2C=1C=CC(=O)N2)O[Si](C(C)(C)C)(C)C.[N:24]([CH2:27][C@@H:28]([C:30]1[CH:35]=[CH:34][C:33]([O:36]CC2C=CC=CC=2)=[C:32]([CH2:44][O:45][Si:46]([C:49]([CH3:52])([CH3:51])[CH3:50])([CH3:48])[CH3:47])[CH:31]=1)[OH:29])=[N+]=[N-]>>[NH2:24][CH2:27][C@@H:28]([C:30]1[CH:35]=[CH:34][C:33]([OH:36])=[C:32]([CH2:44][O:45][Si:46]([C:49]([CH3:52])([CH3:51])[CH3:50])([CH3:47])[CH3:48])[CH:31]=1)[OH:29]

Participants

3

Reactant 2

HCID 58505113(R)-2-Azido-1-[4-(benzyloxy)-3-[[(tert-butyldimethylsilyl)oxy]methyl]phenyl]ethanolHCID 59023604(R)-5-(2-Amino-1-((tert-butyldimethylsilyl)oxy)ethyl)-8-hydroxyquinolin-2(1H)-one

Product 1

HCID 58505193(R)-4-(2-Amino-1-hydroxyethyl)-2-[[(tert-butyldimethylsilyl)oxy]methyl]phenol

Procedure

The title compound was synthesized in a manner analogous to that described in Intermediate 2, using Intermediate 7 as a substrate. ES/MS calcd. for C15H27NNaO3Si+ 320.2. found m/z=320.2 (M+Na)+.

Sources & evidence

ORD record
ord-13c611b8132c4539a7e263009c90bcd6
Source dataset
uspto-grants-2013_02
Patent number
US08367829B2

Reaction notes

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