Sodium Hydroxide → HCID 11496688, compound

HRID 2223771Notes

Reaction equation

HRID 2223771 reaction equation
C([O:9][C@@H:10]1[CH2:17][N:16]2[C@:12]([CH2:29][C:30]3[CH:35]=[CH:34][C:33]([Br:36])=[CH:32][CH:31]=3)([C:13]([CH2:27][CH3:28])=[C:14]([C:19]3[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=3)[C:15]2=[O:18])[CH2:11]1)(=O)C1C=CC=CC=1.[OH-].[Na+]>C1COCC1.CO>[Br:36][C:33]1[CH:32]=[CH:31][C:30]([CH2:29][C@:12]23[C:13]([CH2:27][CH3:28])=[C:14]([C:19]4[CH:20]=[C:21]([Cl:26])[CH:22]=[C:23]([Cl:25])[CH:24]=4)[C:15](=[O:18])[N:16]2[CH2:17][C@@H:10]([OH:9])[CH2:11]3)=[CH:35][CH:34]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 11570605HCID 11570605, compound

Product 1

HCID 11496688HCID 11496688, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

(2S,7aS)-7a-(4-Bromobenzyl)-6-(3,5-dichlorophenyl)-7-ethyl-5-oxo-2,3,5,7a-tetrahydro-1H-pyrrolizin-2-yl benzoate VIIb (5 mg, 0.01 mmol) was suspended in THF (1 mL) and treated with 1N aqueous NaOH (50 uL). The reaction was stirred for 5 h, diluted with MeOH (1 mL) and purified on preparative HPLC using MeOH, H2O, TFA(0.1%) as the eluant to give (6S, 7aS)-7a-(4-Bromobenzyl)-2-(3,5-dichlorophenyl)-1-ethyl-6-hydroxy-5,6,7,7a-tetrahydro-3H-pyrrolizin-3-one VIII, (2 mg, 42%) LCMS, (m/z) 480/482 (M++H), HPLC Retention Time/Condition 1: 2.03 min.

Workup

  1. custompurified on preparative HPLC

Sources & evidence

ORD record
ord-149c9fe3b8ca420294383d3dd2425ca7
Source dataset
uspto-grants-2008_05
Patent number
US07375237B2

Reaction notes

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