Triethylamine → HCID 59374953, compound

HRID 1015514Notes

Reaction equation

HRID 1015514 reaction equation
[OH:1][CH2:2][C:3]12[CH2:11][CH:7]3[CH2:8][CH:9]([CH2:10]1)[C:5]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])([CH2:6]3)[CH2:4]2.CCN(CC)CC.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>C1COCC1.CN(C1C=CN=CC=1)C.O>[CH3:27][S:28]([O:1][CH2:2][C:3]12[CH2:11][CH:7]3[CH2:8][CH:9]([CH2:10]1)[C:5]([NH:12][C:13]([O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:19])([CH2:6]3)[CH2:4]2)(=[O:30])=[O:29]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86761367HCID 86761367, compound

Product 1

HCID 59374953HCID 59374953, compoundYield 99.2%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of tert-butyl [1-(hydroxymethyl)tricyclo[3.3.1.03,7]non-3-yl]carbamate (0.65 g, 2.45 mmol) obtained in step VI in THF (10 mL) at ice bath temperature, was sequentially added Et3N (1.0 mL, 7.35 mmol), DMAP (20 mg, 0.16 mmol), and methanesulfonyl chloride (0.29 mL, 3.7 mmol). After stirring the reaction at the same temperature for 0.5 h, it was diluted with water and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, and the solvent was removed under reduced pressure. The crude product was purified by column chromatography to obtain title compound {3-[(tert-butoxy carbonyl)amino]tricyclo[3.3.1.03,7]non-1-yl}methyl methane sulfonate as a viscous liquid (0.84 g) in 100% yield. m/z (M+1) 358; 1H NMR (CDCl3) 300 MHz δ 4.76 (s (br), 1H), 4.02 (s, 2H), 3.01 (s, 2H), 2.99 (s, 3H), 2.54-2.44 (m, 1H), 2.42-2.35 (m, 1H), 2.20-1.87 (m, 4H), 1.82 (dd, J=2.2, 10.5 Hz, 1H), 1.76-1.58 (m, 4H), 1.57-1.48 (m, 1H), 1.45 (s, 9H).

Workup

  1. customthe reaction at the same temperature for 0.5 h
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. customthe solvent was removed under reduced pressure
  6. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-532dea7ee4b64f648e2e8c1cfbe066a5
Source dataset
uspto-grants-2011_07
Patent number
US07985759B2

Reaction notes

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