Water → HCID 17861996, compound

HRID 1784440Notes

Reaction equation

[CH3:1][N:2]([CH3:30])[C:3]([O:5][C:6]1(O)[CH:15]=[CH:14][C:13]2[CH:12]([CH2:16][C:17](OCC)=[O:18])[N:11]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:10][CH2:9][C:8]=2[CH2:7]1)=[O:4].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH3:30][N:2]([CH3:1])[C:3]([O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH:12]([CH2:16][CH2:17][OH:18])[N:11]([C:22]([O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:23])[CH2:10][CH2:9]2)=[O:4]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of t-butyl 6-dimethylcarbamoyloxy-1-ethoxycarbonylmethyl-6-hydroxy-3,4-dihydro-1H-isoquinoline-2-carboxylate (1.97 g, 4.84 mmol) synthesized in step (e) of Example 187 in tetrahydrofuran (30 ml) was added lithium aluminum hydride (270 mg, 7.2 mmol) at −78° C., and the resulting mixture was stirred for 20 minutes at −78° C. and for 20 minutes at 0° C. successively under a nitrogen atmosphere. After stirring, to the reaction mixture were added water (0.3 ml), 15% aqueous sodium hydroxide solution (0.3 ml) and water (0.9 ml) in this order with stirring, and the resulting mixture was dried over anhydrous sodium sulfate, filtered, and evaporated in vacuo to afford the crude product. The crude product was purified by chromatography on a silica gel column using a mixed solvent of hexane and ethyl acetate (1:1-0:1) as the eluent to afford the title compound (1.38 g, yield: 78%) as a colorless oil.

Workup

stirringAfter stirring, to the reaction mixture
stirringwith stirring
dry with materialthe resulting mixture was dried over anhydrous sodium sulfate
filtrationfiltered
customevaporated in vacuo
customto afford the crude product
customThe crude product was purified by chromatography on a silica gel column

Sources & evidence

ORD record: ord-49eed0ece98a4e43bb1fdcb2d99d8533
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07504393B2

Reaction notes

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