Dibenzylamine → 3-(aminomethyl)-N,N-dibenzyloxetan-3-amine

HRID 1092349Notes

Reaction equation

HRID 1092349 reaction equation
[CH2:1]([N:8]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:9]1([C:13]#[N:14])[CH2:12][O:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CC(=O)C1.C(NCC1C=CC=CC=1)C1C=CC=CC=1.C[Si](C#N)(C)C>CO.[Ni]>[NH2:14][CH2:13][C:9]1([N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12][O:11][CH2:10]1

Participants

7

Reactant 4

HCID 7656DibenzylamineHCID 82115Trimethylsilyl cyanideHCID 150242543-OxetanoneHCID 574159013-(Dibenzylamino)oxetane-3-carbonitrile

Product 1

HCID 574158213-(aminomethyl)-N,N-dibenzyloxetan-3-amineYield 107.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To 3-Dibenzylamino-oxetane-3-carbonitrile (156 mg) (prepared by Strecker synthesis in analogy to example 83/84, step a, from oxetan-3-one, dibenzyl-amine and trimethylsilyl cyanide) in methanol (10 ml) was added a catalytic amount of Raney nickel and the reaction mixture was then stirred at RT under an atmosphere of H2 for 8 h. The catalyst was removed by filtration, the filtrate concentrated under reduced pressure to provide the title compound (170 mg) as off-white solid, MS (ESI): 283.17 (MH+).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-0b55cadd4996454eaa66e0d435f33571
Source dataset
uspto-grants-2012_03
Patent number
US08129423B2

Reaction notes

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