Benzylacetylene → HCID 66706523, compound

HRID 2041105Notes

Reaction equation

HRID 2041105 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[C:15](OS(C(F)(F)F)(=O)=O)=[CH:16][CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:27]1([CH2:33][C:34]#[CH:35])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([C:35]#[C:34][CH2:33][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:16][CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 575753BenzylacetyleneHCID 575058791,1-Dimethylethyl 6-{[(trifluoromethyl)sulfonyl]oxy}-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate

Product 1

HCID 66706523HCID 66706523, compoundYield 74%

Procedure

Use a method similar to the General Procedure 3 to couple 3-tert-butoxycarbonyl-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (0.6 g, 1.5 mmol) with 3-phenyl-1-propyne (0.38 mL, 3 mmol). Purify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 40:1 and 20:1) to give 3-tert-butoxycarbonyl-6-(3-phenyl-prop-1-ynyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine as an orange oil (400 mg, 74%).

Workup

  1. customPurify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 40:1 and 20:1)

Sources & evidence

ORD record
ord-bda2398fb75c4b8e8eb0a927cbe3f837
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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