Aluminium lithium hydride → HCID 69596716, compound

HRID 890318Notes

Reaction equation

HRID 890318 reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][CH2:6][C@H:7]1[CH2:11][CH2:10][C@@H:9]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[N:8]1[S:19]([C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=1)(=[O:21])=[O:20].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[F:18][C:15]1[CH:14]=[CH:13][C:12]([C@H:9]2[N:8]([S:19]([C:22]3[CH:23]=[CH:24][C:25]([CH3:28])=[CH:26][CH:27]=3)(=[O:21])=[O:20])[C@@H:7]([CH2:6][CH2:5][CH2:4][CH2:3][OH:2])[CH2:11][CH2:10]2)=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 69596746HCID 69596746, compound

Product 1

HCID 69596716HCID 69596716, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Reduction of (2S,5S)-4-[5-(4-fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-butyric acid methyl ester with lithium aluminum hydride (1.5 eq.) in THF at RT, aqueous work-up and purification by column chromatography yielded the title compound as a colorless oil, MS: m/e=392.3 (M+H+) and [α]D20=−80.1° (c=1.0870 in chloroform).

Sources & evidence

ORD record
ord-3928213bf51742ef8c2549fc81505eb3
Source dataset
uspto-grants-2006_02
Patent number
US06995182B2

Reaction notes

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