Hydrochloric Acid → tert-butyl N-[(piperidin-3-yl)methyl]carbamate

HRID 2079374노트

반응식

HRID 2079374 반응식
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:3]=1>CO.O=[Pt]=O>[NH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:14])([CH3:13])[CH3:15])[CH2:3]1

참가 물질

5

반응물 2

HCID 313Hydrochloric AcidHCID 13948280tert-Butyl (pyridin-3-ylmethyl)carbamate

생성물 1

HCID 2756030tert-butyl N-[(piperidin-3-yl)methyl]carbamate수율 95%

시약·촉매·용매 2

HCID 345198Adams' catalyst촉매HCID 887Methanol용매2회

실험 절차

A cold solution of HCl in MeOH (prepared by adding acetyl chloride (13.5 mL, 14.9 g, 0.19 mol) to 1 L of MeOH) was added to a cold solution of tert-butyl pyridin-3-ylmethylcarbamate (41.0 grams, 0.20 mol) in MeOH (100 mL). The solution was transferred to a Parr hydrogenation apparatus at 12° C. PtO2 (3 g) was added, and 12 bar pressure of H2 was applied. After 16 hours 1H NMR of a concentrated sample indicated the reaction to be complete. The catalyst was filtered, and conc. aq. NaOH (20 mL) was added to neutralize the HCl. The solution was concentrated to remove the bulk of the MeOH and extracted with tert-butyl methyl ether (4×200 mL). The combined organic layers were washed with saturated aqueous NaCl solution, dried over Na2SO4, and concentrated to give the product (40.16 g, 0.187 mol, 95%) as a yellow oil that crystallized upon standing. 1H NMR (300 MHz, CDCl3): δ 4.62 (bs. s, 1H), 3.06-2.94 (m, 4H), 2.52 (dt, J=12 Hz, 3 Hz, 1H), 2.28 (dd, J=12 Hz, 10 Hz, 1H), 1.82-1.72 (m, 1H), 1.70-1.51 (m, 3H), 1.49-1.34 (m, 1H), 1.42 (s, 9H), 1.06 (dq, J=12 Hz, 4 Hz, 1H) ppm.

후처리

  1. customwas transferred to a Parr hydrogenation apparatus at 12° C
  2. customthe reaction
  3. filtrationThe catalyst was filtered
  4. additionconc. aq. NaOH (20 mL) was added
  5. concentrationThe solution was concentrated
  6. customto remove the bulk of the MeOH
  7. extractionextracted with tert-butyl methyl ether (4×200 mL)
  8. washThe combined organic layers were washed with saturated aqueous NaCl solution
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated

출처 및 근거

ORD 기록
ord-4c5fb3bd0df44a08a2cfe4293f77d568
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07928107B2

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