Diisopropylethylamine → HCID 59437167, compound

HRID 75163Notes

Reaction equation

HRID 75163 reaction equation
[C:1]12([CH2:11][NH:12][C@H:13]([CH3:22])[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(C(C)C)C(C)C.Cl[C:33](Cl)([O:35]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl.CCOCC>[C:1]12([CH2:11][N:12]3[C@H:13]([CH3:22])[C@H:14]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)[O:15][C:33]3=[O:35])[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 68477452HCID 68477452, compound

Product 1

HCID 59437167HCID 59437167, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To an ice-cold, stirred solution of (1S,2R)-2-(1-adamantylmethylamino)-1-phenylpropan-1-ol (715 mg, 2.4 mmol) and DIEA (1.3 mL, 7.2 mmol) in CH2Cl2 (50 mL) was added solid triphosgene (233 mg, 0.79 mmol). The ice bath was allowed to melt and the mixture was stirred at rt for 3 h. The mixture was diluted with ether (150 mL), washed with 5% aq HCl (50 mL) and satd aq NaHCO3 (50 mL), and dried over MgSO4. Removal of the solvent left (4R,5S)-3-((1-adamantyl)methyl)-4-methyl-5-phenyloxazolidin-2-one as a white solid. 1H NMR (CDCl3) 0.76 (d, 3H), 1.5-1.8 (12H), 2.01 (3H), 2.52 (d, 1H), 3.30 (d, 1H), 4.09 (m, 1H), 5.63 (d, 1H), 7.25-7.40 (5H); LC-MS (3 min) tR=2.26 min, m/z=326, 348.

Workup

  1. washwashed with 5% aq HCl (50 mL)
  2. dry with materialdried over MgSO4
  3. customRemoval of the solvent
  4. waitleft (4R,5S)-3-((1-adamantyl)methyl)-4-methyl-5-phenyloxazolidin-2-one as a white solid
  5. customLC-MS (3 min) tR=2.26 min, m/z=326, 348

Sources & evidence

ORD record
ord-3c2627443f2140f986efc8ff2ae6e9b2
Source dataset
uspto-grants-2014_09
Patent number
US08835426B2

Reaction notes

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