Propargyl bromide → 1-(Prop-2-yn-1-yl)pyrrolidine

HRID 720153Notes

Reaction equation

HRID 720153 reaction equation
CO[C:3]([C:5]1[NH:6][C:7]2[CH:8]=[C:9]([NH:19][C:20]([O:22]C(C)(C)C)=O)[CH:10]=[C:11]3[C:17](=[O:18])[NH:16][N:15]=[CH:14][C:13]=1[C:12]=23)=O.[CH2:27]([N:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1)[C:28]#[CH:29].Br[CH2:36]C#C.N1[CH2:43][CH2:42][CH2:41][CH2:40]1.O1[CH2:48][CH2:47][CH2:46][CH2:45]1>C(N(CC)CC)C>[CH2:27]([N:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1)[C:28]#[CH:29].[O:18]=[C:17]1[C:11]2[C:12]3[C:13](=[C:5]([C:3]#[C:28][CH2:27][N:30]4[CH2:34][CH2:33][CH2:32][CH2:31]4)[NH:6][C:7]=3[CH:8]=[C:9]([NH:19][C:20]([C@@H:40]3[CH2:36][C@H:41]3[C:42]3[CH:43]=[CH:48][CH:47]=[CH:46][CH:45]=3)=[O:22])[CH:10]=2)[CH:14]=[N:15][NH:16]1

Participants

8

Reactant 5

HCID 7842Propargyl bromideHCID 8028TetrahydrofuranHCID 31268PyrrolidineHCID 2996161-(Prop-2-yn-1-yl)pyrrolidineHCID 1361816128-tert-Butoxycarbonylamino-6-oxo-5,6-dihydro-1H-[1,2]diazepino[4,5,6-cd]indole-2-carboxylic acid methyl ester

Product 2

HCID 2996161-(Prop-2-yn-1-yl)pyrrolidineHCID 136141754(1r,2r)-2-Phenyl-cyclopropanecarboxylic acid [6-oxo-2-(3-pyrrolidin-1-yl-prop-1-ynyl)-5,6-dihydro-1h-[1,2]diazepino[4,5,6-cd]indol-8-yl]-amide

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Preparation of example 247 from Intermediate 147(d) of Example 147 (300 mg, 0.794 mmol) was carried out in three steps in a manner similar to that described for the preparation of Example 233 except that 1-prop-2-ynyl-pyrrolidine was used instead of dimethyl-prop-2-ynyl-amine in step 1. 1-Prop-2-ynyl-pyrrolidine was prepared by stirring 3-bromo-propyne, pyrrolidine and triethylamine at room temperature in tetrahydrofuran for 2 hours. The title compound (80 mg, 0.177 mmol) was obtained as a yellow powder in 36% overall yield.

Sources & evidence

ORD record
ord-49781bcfde9947c69548695215e46acf
Source dataset
uspto-grants-2006_11
Patent number
US07132533B2

Reaction notes

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