Aluminium lithium hydride → (S)-1-[(3S,4S)-1-Benzyl-3-(3,4-difluoro-phenyl)-piperidin-4-yl]-ethanol

HRID 2191140Notes

Reaction equation

HRID 2191140 reaction equation
C(N1CCC(C(O)C)C(C2C=CC(Cl)=CC=2)C1)C1C=CC=CC=1.[CH2:24]([N:31]1[CH2:36][CH2:35][C@H:34]([C:37](=[O:39])[CH3:38])[C@@H:33]([C:40]2[CH:45]=[CH:44][C:43]([F:46])=[C:42]([F:47])[CH:41]=2)[CH2:32]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>[CH2:24]([N:31]1[CH2:36][CH2:35][C@H:34]([C@@H:37]([OH:39])[CH3:38])[C@@H:33]([C:40]2[CH:45]=[CH:44][C:43]([F:46])=[C:42]([F:47])[CH:41]=2)[CH2:32]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 3

HCID 21226445Aluminium lithium hydrideHCID 594381221-[(3S,4S)-1-Benzyl-3-(3,4-difluoro-phenyl)-piperidin-4-yl]-ethanoneHCID 68475389(RS)-1-[(3SR,4SR)-1-Benzyl-3-(4-chloro-phenyl)-piperidin-4-yl]-ethanol

Product 1

HCID 59438160(S)-1-[(3S,4S)-1-Benzyl-3-(3,4-difluoro-phenyl)-piperidin-4-yl]-ethanol

Procedure

In analogy to the procedure described for the synthesis of (RS)-1-[(3SR,4SR)-1-Benzyl-3-(4-chloro-phenyl)-piperidin-4-yl]-ethanol (example 5 (d)) the title compounds were synthesized from 1-[(3S,4S)-1-Benzyl-3-(3,4-difluoro-phenyl)-piperidin-4-yl]-ethanone through reduction with LiAlH4. (S)-1-[(3S,4S)-1-Benzyl-3-(3,4-difluoro-phenyl)-piperidin-4-yl]-ethanol was obtained as light yellow waxy solid. MS (m/e): 332.1 [(M+H)+] and (R)-1-[(3S,4S)-1-Benzyl-3-(3,4-difluoro-phenyl)-piperidin-4-yl]-ethanol was obtained as light yellow viscous oil. MS (m/e): 332.1 [(M+H)+].

Sources & evidence

ORD record
ord-b47f972f975042adbf213d2d86cae1ae
Source dataset
uspto-grants-2012_12
Patent number
US08324248B2

Reaction notes

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