3-Chloro-2,2-dimethylpropanoyl chloride → HCID 58379695, compound

HRID 1038989Notes

Reaction equation

HRID 1038989 reaction equation
[CH2:1]([NH:4][C@H:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6]1)[CH:2]=[CH2:3].[Cl:14][CH2:15][C:16]([CH3:21])([CH3:20])[C:17](Cl)=[O:18]>C(Cl)Cl>[CH2:1]([N:4]([C@H:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6]1)[C:17](=[O:18])[C:16]([CH3:21])([CH3:20])[CH2:15][Cl:14])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 613453-Chloro-2,2-dimethylpropanoyl chlorideHCID 5326779(R)-N-Allyl-1-aminoindane

Product 1

HCID 58379695HCID 58379695, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the DCM solution of (1R) —N-allylindan-1-amine (prepared in Step A), cooled to −20° C., was added 3-chloro-2,2-dimethylpropanoyl chloride (872 mg, 5.63 mmol). After allowing the reaction to sit at −20° C. for 14 hours LCMS analysis indicated a complete consumption of secondary amine. The reaction mixture was then concentrated in vacuo to a reasonable volume of DCM. This DCM solution was then applied to a silica gel column for purification, eluting with a gradient of 10-50% EtOAc in hexanes to give the title compound. MS: m/z=314 (M+23).

Workup

  1. customthe reaction
  2. customa complete consumption of secondary amine
  3. concentrationThe reaction mixture was then concentrated in vacuo to a reasonable volume of DCM
  4. customThis DCM solution was then applied to a silica gel column for purification
  5. washeluting with a gradient of 10-50% EtOAc in hexanes

Sources & evidence

ORD record
ord-55d36681d36d48939264264edebd345f
Source dataset
uspto-grants-2013_10
Patent number
US08552023B2

Reaction notes

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