Trifluoroacetic acid → (1R)-2-azido-1-(4-(2-methylpentyloxy)phenyl)ethanamine

HRID 1874626Notes

Reaction equation

HRID 1874626 reaction equation
[N:1]([CH2:4][C@H:5]([NH:19]C(=O)OC(C)(C)C)[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH:14]([CH3:18])[CH2:15][CH2:16][CH3:17])=[CH:8][CH:7]=1)=[N+:2]=[N-:3].FC(F)(F)C(O)=O>ClCCl>[N:1]([CH2:4][C@@H:5]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH:14]([CH3:18])[CH2:15][CH2:16][CH3:17])=[CH:8][CH:7]=1)[NH2:19])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86658397t-butyl (1R)-2-azido-1-(4-(2-methylpentyloxy)phenyl)ethylcarbamate

Product 1

HCID 86658398(1R)-2-azido-1-(4-(2-methylpentyloxy)phenyl)ethanamineYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of t-butyl (1R)-2-azido-1-(4-(2-methylpentyloxy)phenyl)ethylcarbamate (14.2 g, 39.2 mmol) in dichloromethane (2 mL) was added trifluoroacetic acid (18.1 mL, 235 mmol). The reaction mixture was stirred at room temperature for 1 h. The mixture was concentrated and the residue was transferred to a separatory funnel containing saturated aqueous K2CO3 solution. The aqueous layer was extracted with ethyl acetate (3×50 mL). The combined organic layers were dried over MgSO4, filtered and concentrated to afford (1R)-2-azido-1-(4-(2-methylpentyloxy)phenyl)ethanamine (9 g, 88% yield) as a yellow oil: 1H NMR (400 MHz, DMSO-d6) δ 7.29 (d, J=8.8 Hz, 2H), 6.88 (d, J=8.6 Hz, 2 H), 3.96 (t, J=6.4 Hz, 1H), 3.80 (dd, J=9.1, 5.5 Hz, 1H), 3.71 (dd, J=9.2, 6.7 Hz, 1H), 3.29-3.39 (m, 2H), 2.59-2.75 (m, 2H), 1.86 (dq, J=12.8, 6.5 Hz, 1H), 1.25-1.48 (m, 3H), 1.12-1.22 (m, 1H), 0.95 (d, J=6.8 Hz, 3H), 0.88 (t, J=7.1 Hz, 3H); HRMS (ESI) m/e 263.1860 [(M+H)+, calcd for C14H23N4O 263.1872].

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was transferred to a separatory funnel
  3. additioncontaining saturated aqueous K2CO3 solution
  4. extractionThe aqueous layer was extracted with ethyl acetate (3×50 mL)
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-216e6f592352476fb7f3f0ff6f6fc6a1
Source dataset
uspto-grants-2012_11
Patent number
US08304577B2

Reaction notes

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