Ammonium Chloride → HCID 86736890, compound

HRID 1701522Notes

Reaction equation

HRID 1701522 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[C@@H:14]2[C@@H:9]([C:10](=[O:15])[CH2:11][CH2:12][CH2:13]2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].[Li].[Cl-].[NH4+]>O1CCCC1>[CH2:1]([O:3][C:4]([N:6]1[CH:14]2[CH:9]([CH:10]([OH:15])[CH2:11][CH2:12][CH2:13]2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 3028194LithiumHCID 67233711Ethyl (3aS,7aS)-4-oxooctahydro-1H-indole-1-carboxylate

Product 1

HCID 86736890HCID 86736890, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 25.8 g cis-perhydro-4-oxo-1-indoline carboxylic acid ethyl ester in 200 ml absolute tetrahydrofuran is added at -30° to -40° to 1 mole of lithium 3,4-dimethoxyphenylacetylide in tetrahydrofuran (formed from 2 moles 2 molar butyl lithium in hexane and 1 mole 1-(2,2-dibromovinyl)-3,4-dimethoxybenzene in 300 ml benzene at -70°). The mixture is stirred over-night. 100 ml concentrated ammonium chloride solution is added with ice cooling. The organic phase is worked up to give (3aRS,4RS,7aRS)-4-(3,4-dimethoxy)-phenylethinyl)-hexahydro-4-hydroxy-1-indoline carboxylic acid ethyl ester; M.Pt. 153°-155° (from ether).

Sources & evidence

ORD record
ord-ac7790ee8f91491ba8c8cc278afcbb79
Source dataset
uspto-grants-1980_03
Patent number
US04194002

Reaction notes

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