HCID 69657893, compound → HCID 20795049, compound

HRID 1796706Notes

Reaction equation

HRID 1796706 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]([CH2:22][OH:23])[O:14]3)[CH2:11][CH2:10][CH:9]1O)=O)(C)(C)C>ClC1C=CC=CC=1Cl>[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]([CH2:22][OH:23])[O:14]3)[CH:11]=[CH:10][CH:9]=1

Participants

3

Reactant 1

HCID 69657893HCID 69657893, compound

Product 1

HCID 20795049HCID 20795049, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

A solution of (6S)-2-hydroxy-6-hydroxymethyl-3,4,7,8-tetrahydro-2H,6H-5-oxa-1-aza-phenanthrene-1-carboxylic acid tert-butyl ester (0.33 mg, 1.0 mmole) in o-dichlorobenzene (15 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 (50% methylene chloride/hexane) to afford 0.15 g (71%) of the title compound as a solid, mp 128° C., [α]25D=+74.19° (c=7.7, DMSO).

Workup

  1. customThe solvent was removed in vacuum
  2. customThe residue was purified by column chromatography on silica gel (50% methylene chloride/hexane)

Sources & evidence

ORD record
ord-0637ceefd4c44170848acfc96489f541
Source dataset
uspto-grants-2006_04
Patent number
US07030245B2

Reaction notes

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