(S)-(9H-fluoren-9-yl)methyl 1-(benzyl(2,2-diethoxyethyl)amino)-1-oxopropan-2-ylcarbamate → (S)-2-amino-N-benzyl-N-(2,2-diethoxyethyl)propanamide

HRID 576870Notes

Reaction equation

HRID 576870 reaction equation
[CH2:1]([N:8]([CH2:31][CH:32]([O:36][CH2:37][CH3:38])[O:33][CH2:34][CH3:35])[C:9](=[O:30])[C@@H:10]([NH:12]C(=O)OCC1C2C=CC=CC=2C2C1=CC=CC=2)[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1CCCCC1.ClCCl>>[NH2:12][C@@H:10]([CH3:11])[C:9]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:31][CH:32]([O:36][CH2:37][CH3:38])[O:33][CH2:34][CH3:35])=[O:30]

Participants

3

Reactant 2

HCID 66978027(S)-(9H-fluoren-9-yl)methyl 1-(benzyl(2,2-diethoxyethyl)amino)-1-oxopropan-2-ylcarbamateHCID 67144590Dichloromethane piperidine

Product 1

HCID 66644890(S)-2-amino-N-benzyl-N-(2,2-diethoxyethyl)propanamideYield 103.5%

Procedure

To (S)-(9H-fluoren-9-yl)methyl 1-(benzyl(2,2-diethoxyethyl)amino)-1-oxopropan-2-ylcarbamate (Compound XV-1) 1.12 g (2.1 mmol), 25%-piperidine/dichloromethane 16 ml was added and the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated in vacuo and the residue was purified on silica gel column chromatography (n-hexane:ethyl acetate=100:0 to 70:30, chloroform:methanol=100:0 to 80:20) to obtain the title compound 640 mg (yield 100%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was purified on silica gel column chromatography (n-hexane:ethyl acetate=100:0 to 70:30, chloroform:methanol=100:0 to 80:20)

Sources & evidence

ORD record
ord-65c3be958e404e58b3a1a1ac87e790db
Source dataset
uspto-grants-2015_05
Patent number
US09040531B2

Reaction notes

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