1,3,5-Tribromobenzene → HCID 22881076, compound

HRID 725950Notes

Reaction equation

HRID 725950 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][C@H:13]([O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[CH2:12][C@H:9]1[CH:10]=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:23][C:24]1[CH:29]=[C:28](Br)[CH:27]=[C:26]([Br:31])[CH:25]=1>>[C:1]([O:5][C:6]([N:8]1[CH2:14][C@H:13]([O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:17])[CH3:18])[CH2:12][C@H:9]1[CH:10]([OH:11])[C:28]1[CH:29]=[C:24]([Br:23])[CH:25]=[C:26]([Br:31])[CH:27]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 122791,3,5-TribromobenzeneHCID 10969557tert-Butyl (2S,4R)-4-((tert-butyldimethylsilyl)oxy)-2-formylpyrrolidine-1-carboxylate

Product 1

HCID 22881076HCID 22881076, compoundYield 57%

Procedure

(2S,4R)-N-t-Butoxycarbonyl-4-t-butyldimethylsiloxy-2-(α-hydroxy-3,5-dibromobenzyl)pyrrolidine (19.6 g, yield: 56.9%) was prepared as a yellow oily substance, from (2S,4R)-N-t-butoxycarbonyl-4-(t-butyldimethylsiloxy)prolinal (20 g, 60.8 mmol), 1,3,5-tribromobenzene (19.13 g, 60.8 mmol) and 1.6M n-butyl lithium-hexane solution (49.4 ml, 79.04 mmol), in the same manner as in Reference Example 111-1.

Sources & evidence

ORD record
ord-83d05284e60340698f8624c8c0edc07e
Source dataset
uspto-grants-1998_01
Patent number
US05707987

Reaction notes

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