Triethylamine → 4-(1,1,1-Trifluoropropan-2-yl)oxazolidin-2-one

HRID 57340Notes

Reaction equation

HRID 57340 reaction equation
[NH2:1][CH:2]([CH:5]([CH3:10])[C:6]([F:9])([F:8])[F:7])[CH2:3][OH:4].C(N(CC)CC)C.Cl[C:19](Cl)([O:21]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[F:7][C:6]([F:9])([F:8])[CH:5]([CH:2]1[CH2:3][O:4][C:19](=[O:21])[NH:1]1)[CH3:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 98774442-Amino-4,4,4-trifluoro-3-methylbutan-1-ol

Product 1

HCID 904145974-(1,1,1-Trifluoropropan-2-yl)oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-amino-4,4,4-trifluoro-3-methylbutan-1-ol (580 mg, 3.69 mmol) in DCM (13 ml) was added triethylamine (1.132 ml, 8.12 mmol) and added dropwise a solution of triphosgene (329 mg, 1.107 mmol) in 1 mL in DCM (3 ml) over 10 min. The reaction mixture was washed with sat. NH4Cl solution (13 ml) dry, and concentrated in vacuo. Afforded 450 mg (It yellow solid). Used crude in the next step. 1H NMR (400 MHz, CDCl3) b 5.91 (d, J=13.3 Hz, 1H), 4.61-4.34 (m, 1H), 4.22-4.00 (m, 2H), 3.05 (q, J=7.3 Hz, 1H), 2.54-2.14 (m, 1H), 1.34 (t, J=7.3 Hz, 1H), 1.17 (d, J=7.1 Hz, 2H), 1.09 (d, J=7.1 Hz, 1H). MS 183.0507 m/z.

Workup

  1. washThe reaction mixture was washed with sat. NH4Cl solution (13 ml)
  2. customdry
  3. concentrationconcentrated in vacuo
  4. customAfforded 450 mg (It yellow solid)

Sources & evidence

ORD record
ord-a96664db53024588878304f0b7bf73c2
Source dataset
uspto-grants-2016_09
Patent number
US09434719B2

Reaction notes

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