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

HRID 2191111Notes

Reaction equation

HRID 2191111 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]([OH:16])[CH3:15])[CH:10]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1CC[C@H](C(=O)C)[C@@H](C2C=CC(Cl)=CC=2)C1)C1C=CC=CC=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>[CH2:1]([N:8]1[CH2:13][CH2:12][C@H:11]([C@H:14]([OH:16])[CH3:15])[C@@H:10]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 21226445Aluminium lithium hydrideHCID 594381311-[(3S,4S)-1-Benzyl-3-(4-chloro-phenyl)-piperidin-4-yl]-ethanoneHCID 68475389(RS)-1-[(3SR,4SR)-1-Benzyl-3-(4-chloro-phenyl)-piperidin-4-yl]-ethanol

Product 1

HCID 59438191(R)-1-[(3S,4S)-1-Benzyl-3-(4-chloro-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-(4-chloro-phenyl)-piperidin-4-yl]-ethanone through reduction with LiAlH4. (R)-1-[(3S,4S)-1-Benzyl-3-(4-chloro-phenyl)-piperidin-4-yl]-ethanol was obtained as light yellow viscous oil. MS (m/e): 330.1 [(M+H)+] and (S)-1-[(3S,4S)-1-Benzyl-3-(4-chloro-phenyl)-piperidin-4-yl]-ethanol was obtained as colorless foam. MS (m/e): 330.1 [(M+H)+]

Sources & evidence

ORD record
ord-9cbdeecc58f041fb9d0103b7ad13e6aa
Source dataset
uspto-grants-2012_12
Patent number
US08324248B2

Reaction notes

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