Lithium borohydride → tert-butyl (3RS,4RS)-3-(4-benzyloxy-naphthalen-2-ylmethoxy)-4-(3-hydroxymethyl-phenyl)-piperidine-1-carboxylate

HRID 1005002Notes

Reaction equation

HRID 1005002 reaction equation
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[C:11]([CH2:19][O:20][CH:21]2[CH:26]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([C:33](OC)=[O:34])[CH:28]=3)[CH2:25][CH2:24][N:23]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:22]2)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Li+]>>[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[C:11]([CH2:19][O:20][CH:21]2[CH:26]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([CH2:33][OH:34])[CH:28]=3)[CH2:25][CH2:24][N:23]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:22]2)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 4148881Lithium borohydrideHCID 54179161HCID 54179161, compound

Product 1

HCID 54536116tert-butyl (3RS,4RS)-3-(4-benzyloxy-naphthalen-2-ylmethoxy)-4-(3-hydroxymethyl-phenyl)-piperidine-1-carboxylate

Procedure

In an analogous manner to that described in Example 22(e), by reducing tert-butyl (3RS,4RS)-3-(4-benzyloxy-naphthalen-2-ylmethoxy)-4-(3-methoxycarbonyl-phenyl)-piperidine-1-carboxylate with lithium borohydride there was obtained tert-butyl (3RS,4RS)-3-(4-benzyloxy-naphthalen-2-ylmethoxy)-4-(3-hydroxymethyl-phenyl)-piperidine-1-carboxylate as a colourless solid; MS: 554 (M+H)+.

Sources & evidence

ORD record
ord-f071ec7616a04d268d67ba38a739f03c
Source dataset
uspto-grants-2000_04
Patent number
US06051712

Reaction notes

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