Trifluoroacetic acid → (S,Z)-3-amino-1-benzyl-3,4,7,8-tetrahydroazocin-2(1H)-one

HRID 529509Notes

Reaction equation

HRID 529509 reaction equation
[CH2:1]([N:8]1[CH2:15][CH2:14][CH:13]=[CH:12][CH2:11][C@H:10]([NH:16]C(=O)OC(C)(C)C)[C:9]1=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:16][C@H:10]1[CH2:11][CH:12]=[CH:13][CH2:14][CH2:15][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:9]1=[O:24]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68292616(S,Z)-tert-butyl 1-benzyl-2-oxo-1,2,3,4,7,8-hexahydroazocin-3-ylcarbamate

Product 1

HCID 68292242(S,Z)-3-amino-1-benzyl-3,4,7,8-tetrahydroazocin-2(1H)-oneYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S,Z)-tert-butyl 1-benzyl-2-oxo-1,2,3,4,7,8-hexahydroazocin-3-ylcarbamate (10 mg, 0.030 mmol) in DCM (0.2 mL) at rt was added TFA (0.2 mL). The clear solution was stirred at rt for 40 min. The reaction mixture was concentrated and dried in vacuum to give (S,Z)-3-amino-1-benzyl-3,4,7,8-tetrahydroazocin-2(1H)-one (7.0 mg, 0.030 mmol, 100% yield) as an oil. Anal. Calcd. for C14H18N2O m/z 230.3. found: 231.1 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customdried in vacuum

Sources & evidence

ORD record
ord-0aa2ce53ad6f4eaeaab01d048411e8b4
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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