Triethylamine → 1225228-92-1

HRID 709845Notes

Reaction equation

HRID 709845 reaction equation
[NH2:1][C:2]([CH:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:16][CH3:17])[CH:12]=2)[CH2:7]1)([CH3:5])[CH2:3][OH:4].C(N(CC)CC)C.Cl[C:26](Cl)([O:28]C(=O)OC(Cl)(Cl)Cl)Cl>ClCCl>[CH3:17][O:16][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH:6]([C:2]1([CH3:5])[CH2:3][O:4][C:26](=[O:28])[NH:1]1)[CH2:15][CH2:14]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 461946762-Amino-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)propan-1-ol

Product 1

HCID 461946751225228-92-1Yield 54.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To 25 grams of 2-amino-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)propan-1-ol in 575 mL of dichloromethane was added 45 g of triethylamine. The mixture was cooled to 0° C., and kept below 5° C. while 21 g of triphosgene in dichloromethane was added dropwise. The mixture was stirred at 20-25° C. for 1.5 hrs. The reaction was followed by HPLC until the starting material disappeared. The mixture was concentrated under reduced pressure, 375 mL ethyl acetate was added to the residue. It was washed with water (50 mL×2), dried, decolorized with carbon, and concentrated and dried to afford 10 g of 4-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-4-methyloxazolidin-2-one, M=261, purity 97%.

Workup

  1. additionwas added dropwise
  2. concentrationThe mixture was concentrated under reduced pressure, 375 mL ethyl acetate
  3. additionwas added to the residue
  4. washIt was washed with water (50 mL×2)
  5. customdried
  6. concentrationconcentrated
  7. customdried

Sources & evidence

ORD record
ord-1a000f0120494f02bf6aed2cc66197cf
Source dataset
uspto-grants-2015_11
Patent number
US09181191B2

Reaction notes

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