HCID 131724982, compound → HCID 131724983, compound

HRID 1796711Notes

Reaction equation

HRID 1796711 reaction equation
C(OC([N:8]1[C:21]2[C:12](=[C:13]3[C:18](=[CH:19][CH:20]=2)[CH2:17][CH2:16][C@H:15]([C:22]([CH3:30])([CH3:29])[O:23][SiH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])[O:14]3)[CH2:11][CH2:10][CH:9]1O)=O)(C)(C)C>ClC1C=CC=CC=1Cl>[C:25]([SiH2:24][O:23][C:22]([CH3:30])([CH3:29])[C@H:15]1[CH2:16][CH2:17][C:18]2[C:13](=[C:12]3[C:21](=[CH:20][CH:19]=2)[N:8]=[CH:9][CH:10]=[CH:11]3)[O:14]1)([CH3:28])([CH3:26])[CH3:27]

Participants

3

Reactant 1

HCID 131724982HCID 131724982, compound

Product 1

HCID 131724983HCID 131724983, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

A solution of (6R)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-hydroxy-3,4,7,8-tetrahydro-2H,6H-5-oxa-1-aza-phenanthrene-1-carboxylic acid tert-butyl ester (0.45 g, 1.0 mmole) in o-dichlorobenzene (150 mL) was stirred at 180° C. for 4 hours. The solvent was removed in vacuum. The residue was purified by column chromatography on silica gel (10% methylene chloride/hexane) to afford 0.23 g (70%) of the title compound as an oil, [α]25D=−61.94° (c=10.7, THF).

Workup

  1. customThe solvent was removed in vacuum
  2. customThe residue was purified by column chromatography on silica gel (10% methylene chloride/hexane)

Sources & evidence

ORD record
ord-4533dc3de6aa46e397973c18e9391648
Source dataset
uspto-grants-2006_04
Patent number
US07030245B2

Reaction notes

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