Triethylamine → HCID 59437177, compound

HRID 75156Notes

Reaction equation

HRID 75156 reaction equation
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[C:13]12([CH2:23][NH:24][CH2:25][CH2:26][CH:27]([OH:32])[CH2:28][CH:29]([CH3:31])[CH3:30])[CH2:22][CH:17]3[CH2:18][CH:19]([CH2:21][CH:15]([CH2:16]3)[CH2:14]1)[CH2:20]2.CCN(CC)CC>C(Cl)Cl>[C:13]12([CH2:23][N:24]3[CH2:25][CH2:26][CH:27]([CH2:28][CH:29]([CH3:30])[CH3:31])[O:32][C:2]3=[O:4])[CH2:22][CH:17]3[CH2:18][CH:19]([CH2:21][CH:15]([CH2:16]3)[CH2:14]1)[CH2:20]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 594371801-(1-Adamantylmethylamino)-5-methylhexan-3-ol

Product 1

HCID 59437177HCID 59437177, compoundYield 218.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of triphosgene (35 mg, 0.12 mmol) in anhydrous CH2Cl2 (500 μL) was added slowly to a solution of 1-(1-adamantylmethylamino)-5-methylhexan-3-ol (100 mg, 0.36 mmol) and Et3N (50 μl, 0.257 mmol) in anhydrous CH2Cl2 (2 mL) at 0° C. The reaction mixture was stirred for 1 h. Solvent was removed and the residue was purified by preparative TLC to give 3-((1-adamantyl)methyl)-6-isobutyl-1,3-oxazinan-2-one (80 mg, 74%). 1H NMR (MeOD, 400 MHZ): δ=0.93-0.98 (q, 6H), 1.35-1.44 (m, 1H), 1.50-2.08 (m, 18H), 2.87-2.94 (d, 1H), 3.12-3.20 (d, 1H), 3.30-3.40 (m, 1H), 3.49-3.61 (m, 1H), 4.35-4.45 (m, 1H); MS m/z=306.

Workup

  1. customSolvent was removed
  2. customthe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-4dcf967124bd4126acd4c88c863d2053
Source dataset
uspto-grants-2014_09
Patent number
US08835426B2

Reaction notes

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