[7-[2-(3-Chlorophenyl)ethynyl]-9-oxa-3,8-diazaspiro[4.4]non-7-en-3-yl]-pyrrolidin-1-yl-methanone → [2-[2-(3-Chlorophenyl)ethynyl]-4-oxa-3,8-diazaspiro[4.5]dec-2-en-8-yl]-pyrrolidin-1-yl-methanone

HRID 2040912Notes

Reaction equation

HRID 2040912 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[CH2:11][C:12]3([O:24][N:25]=2)[CH2:16][CH2:15][N:14]([C:17]([N:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)=[O:18])[CH2:13]3)[CH:5]=[CH:6][CH:7]=1.Cl[C:27]1C=C(C#CC2CC3(CCN(C(OC(C)(C)C)=O)C3)ON=2)C=CC=1>>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[CH2:11][C:12]3([CH2:27][CH2:13][N:14]([C:17]([N:19]4[CH2:20][CH2:21][CH2:22][CH2:23]4)=[O:18])[CH2:15][CH2:16]3)[O:24][N:25]=2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 57493783[7-[2-(3-Chlorophenyl)ethynyl]-9-oxa-3,8-diazaspiro[4.4]non-7-en-3-yl]-pyrrolidin-1-yl-methanoneHCID 57493821Tert-butyl 3-[(3-chlorophenyl)ethynyl]-1-oxa-2,7-diazaspiro[4.4]non-2-ene-7-carboxylate

Product 1

HCID 56644864[2-[2-(3-Chlorophenyl)ethynyl]-4-oxa-3,8-diazaspiro[4.5]dec-2-en-8-yl]-pyrrolidin-1-yl-methanone

Procedure

The title compound was synthesized following the method herein described for the compound of Example 106 but replacing Compound 22d for Compound 27c. After the usual work-up procedure the crude was purified by means of automated flash chromatography (Isolera®TM-Biotage; gradient Petroleum Ether-EtOAc from 7:3 to 3:7) giving 52 mg of the title compound giving pale yellow solid. Yield: 72.6%.

Workup

  1. customThe title compound was synthesized
  2. customAfter the usual work-up procedure the crude was purified by means of automated flash chromatography (Isolera®TM-Biotage; gradient Petroleum Ether-EtOAc from 7:3 to 3:7)

Sources & evidence

ORD record
ord-794ac537da0c4334831af7f50c8e70b4
Source dataset
uspto-grants-2013_11
Patent number
US08580962B2

Reaction notes

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