Triethylamine → HCID 59437182, compound

HRID 75166Notes

Reaction equation

HRID 75166 reaction equation
[C:1]12([CH2:11][NH:12][CH2:13][CH2:14][CH:15]([OH:17])[CH3:16])[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:26](Cl)([O:28]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[C:1]12([CH2:11][N:12]3[CH2:13][CH2:14][CH:15]([CH3:16])[O:17][C:26]3=[O:28])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 59437169HCID 59437169, compound

Product 1

HCID 59437182HCID 59437182, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-(1-adamantylmethylamino)butan-2-ol (50 mg, 0.21 mmol) and Et3N (42.4 mg, 0.42 mmol) in CH2Cl2 (5 mL) at 0° C. under N2, a solution of triphosgene (25 mg, 0.084 mmol) in CH2Cl2 (1 mL) was added dropwise. The mixture was stirred at rt for 1 h. The mixture was concentrated to give crude product, which was purified by preparative TLC to afford 3-((1-adamantyl)methyl)-6-methyl-1,3-oxazinan-2-one (12 mg, 21%). 1H NMR (CD3OD, 400 MHZ): δ=1.46 (d, 3H), 1.72˜2.18 (m, 17H), 3.02 (d, 1H), 3.34 (d, 1H), 3.44 (m, 1H), 3.63 (m, 1H), 4.58 (m, 1H); MS m/z=264

Workup

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

Sources & evidence

ORD record
ord-21792e1b24864b84b5494cc282aacb61
Source dataset
uspto-grants-2014_09
Patent number
US08835426B2

Reaction notes

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