Triethylamine → HCID 59437183, compound

HRID 75144Notes

Reaction equation

HRID 75144 reaction equation
[C:1]12([CH2:11][NH:12][CH2:13][C@H:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[OH:15])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.CCN(CC)CC.Cl[C:30](Cl)([O:32]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[C:1]12([CH2:11][N:12]3[CH2:13][C@H:14]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)[O:15][C:30]3=[O:32])[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 8259841HCID 8259841, compound

Product 1

HCID 59437183HCID 59437183, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-2-((1-adamantylmethyl)amino)-1-phenylethanol (35 mg, 0.12 mmol), Et3N (24.8 mg, 0.25 mmol) in CH2Cl2 (2 mL) at 0° C. was added triphosgene (14.6 mg, 0.05 mmol) and the mixture was stirred for 30 min. The mixture was concentrated under vacuum to give the crude product, which was purified by preparative TLC to give (S)-3-((1-adamantyl)methyl)-5-phenyloxazolidin-2-one (10 mg, 26%). 1H NMR (MeOD, 400 MHZ): δ=1.51-1.95 (m, 15H), 2.89 (q, 2H), 3.55 (q, 1H), 4.10 (t, 1H), 5.57 (q, 1H), 7.34˜7.45 (m, 5H); MS m/z=312.

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. customto give the crude product, which
  3. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-d8cc0911159d49528e5f1f41736ad0f0
Source dataset
uspto-grants-2014_09
Patent number
US08835426B2

Reaction notes

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