Cyclopentylacetylene → Tert-butyl 3-(3-(cyclopentylethynyl)phenyl)-3-hydroxypropylcarbamate

HRID 658822Notes

Reaction equation

HRID 658822 reaction equation
[C:1]([CH:3]1[CH2:7][CH2:6][CH2:5][CH2:4]1)#[CH:2].Br[C:9]1[CH:10]=[C:11]([CH:15]([OH:26])[CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH:12]=[CH:13][CH:14]=1>>[CH:3]1([C:1]#[C:2][C:9]2[CH:10]=[C:11]([CH:15]([OH:26])[CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:24])[CH3:23])[CH:12]=[CH:13][CH:14]=2)[CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

3

Reactant 2

HCID 136725CyclopentylacetyleneHCID 57608439Tert-butyl 3-(3-bromophenyl)-3-hydroxypropylcarbamate

Product 1

HCID 57608534Tert-butyl 3-(3-(cyclopentylethynyl)phenyl)-3-hydroxypropylcarbamate

Procedure

Coupling of ethynylcyclopentane (40) with tert-butyl 3-(3-bromophenyl)-3-hydroxypropylcarbamate (39) following the method used in the synthesis of Example 13 gave tert-butyl 3-(3-(cyclopentylethynyl)phenyl)-3-hydroxypropylcarbamate (41) as a brown oil. Yield (0.386 g, 92%).

Workup

  1. customused in the synthesis of Example 13

Sources & evidence

ORD record
ord-75c8daafdd31457ba7f43857c88ef301
Source dataset
uspto-grants-2011_12
Patent number
US08076516B2

Reaction notes

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