Cyclopropanemethanamine → HCID 58982061, compound

HRID 2242207Notes

Reaction equation

HRID 2242207 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:19]3[CH:18]=[CH:17][C:16]4[CH2:20][CH2:21][C:22](=O)[CH2:23][C:15]=4[C:14]=3[CH:13]=[CH:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH2:25][CH2:26][CH:27]1[CH2:29][CH2:28]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH:27]1([CH2:26][NH:25][CH:22]2[CH2:23][C:15]3[C:14]4[CH:13]=[CH:12][N:11]([S:8]([C:5]5[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=5)(=[O:10])=[O:9])[C:19]=4[CH:18]=[CH:17][C:16]=3[CH2:20][CH2:21]2)[CH2:29][CH2:28]1

Participants

5

Reactant 3

HCID 75646CyclopropanemethanamineHCID 5049666Sodium triacetoxyborohydrideHCID 10404932HCID 10404932, compound

Product 1

HCID 58982061HCID 58982061, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-[(4-methylphenyl)sulfonyl]-6,7,8,9-tetrahydro-3H-benzo[e]indol-8-one (2.0 g) in CH2Cl2 is treated sequentially with aminomethylcyclopropane ((0.630 g, 1.5 eq.) and sodium triacetoxyborohydride (1.6 g, 1.3 eq.), stirred at room temperature for 16 h, quenched with 1N NaOH and extracted with CH2Cl2. The extracts are combined, dried over MgSO4 and concentrated in vacuo to give the title product, 2.2 g, identified by NMR and mass spectral analyses.

Workup

  1. customquenched with 1N NaOH
  2. extractionextracted with CH2Cl2
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b085d6e55be34a6482c3282855f0f4d6
Source dataset
uspto-grants-2010_03
Patent number
US07671079B2

Reaction notes

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