Boron Trichloride → HCID 57516532, compound

HRID 1909115Notes

Reaction equation

HRID 1909115 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C@H:7]([NH:9]C(=O)OCC2C=CC=CC=2)[CH3:8])[N:3]=1.B(Cl)(Cl)Cl>ClCCl>[CH3:1][C:2]1[O:6][N:5]=[C:4]([C@H:7]([NH2:9])[CH3:8])[N:3]=1

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 86657028HCID 86657028, compound

Product 1

HCID 57516532HCID 57516532, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of benzyl [(1R)-1-(5-methyl-1,2,4-oxadiazol-3-yl)ethyl]carbamate (1.10 g, 4.21 mmol) in dichloromethane (40 mL) was added 1 M boron trichloride solution in dichloromethane (21.1 mL, 21.1 mmol) at 0° C. The reaction mixture was allowed to warm from 0° C. to 20° C. over 4 h. The solution was quenched by 5 ml of methanol at 0° C. After warming to ambient temperature, the mixture was concentrated and the residue was washed with 100 mL of diethyl ether (2×) to give the hydrochloride salt of (1R)-1-(5-methyl-1,2,4-oxadiazol-3-yl)ethanamine was obtained as solid (0.84 g). 1H NMR (500 MHz, CD3OD): δ 4.70-4.61 (m, 1H); 2.63 (s, 3H); 1.67 (d, J=6.9 Hz, 3H).

Workup

  1. temperatureto warm from 0° C. to 20° C. over 4 h
  2. customThe solution was quenched by 5 ml of methanol at 0° C
  3. concentrationthe mixture was concentrated
  4. washthe residue was washed with 100 mL of diethyl ether (2×)

Sources & evidence

ORD record
ord-5aa30dde696d4a0e8b405f64187785c1
Source dataset
uspto-grants-2013_12
Patent number
US08598209B2

Reaction notes

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