tert-Butanol → benzyl (2S,5R)-5-((tert-butoxycarbonyl)amino)-2-methylpiperidine-1-carboxylate

HRID 2367419노트

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HRID 2367419 반응식
[CH3:1][C@H:2]1[N:7]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:6][C@@H:5](C(O)=O)[CH2:4][CH2:3]1.[C:21]([OH:25])([CH3:24])([CH3:23])[CH3:22].C([N:28]([CH2:31]C)CC)C.P(N=[N+]=[N-])(OC1C=CC=CC=1)(OC1C=CC=CC=1)=[O:34]>>[C:12]1([CH2:11][O:10][C:8]([N:7]2[CH2:6][C@H:5]([NH:28][C:31]([O:25][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:34])[CH2:4][CH2:3][C@@H:2]2[CH3:1])=[O:9])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

참가 물질

5

반응물 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 123414Diphenylphosphoryl azideHCID 51357693(3S,6R)-1-((benzyloxy)carbonyl)-6-methylpiperidine-3-carboxylic acid

생성물 1

HCID 51354040benzyl (2S,5R)-5-((tert-butoxycarbonyl)amino)-2-methylpiperidine-1-carboxylate수율 35.2%

실험 절차

cis-6-methyl-1-{[(phenylmethyl)oxy]carbonyl}-3-piperidinecarboxylic acid (2.62 g, 9.45 mmol) was dissolved in t-butyl alcohol (20 mL, 212 mmol) (anhydrous) in a 40 mL vial. Triethylamine (1.975 mL, 14.17 mmol) was added, followed by the slow addition of diphenyl azidophosphate (dppa) (1.87 mL, 8.65 mmol) at room temperature. The reaction was stirred at room temperature for 30 minutes, and then heated at 100° C. overnight. The reaction mixture was concentrated, and then redissolved with 150 mL of EtOAc. The resulting organic mixture was washed with water (50 mL), brine, dried (Na2SO4), filtered, and concentrated. The resulting clear oil was purified in 50 g Biotage SNAP column with gradient of 0 to 50% of EtOAc in Hexane over 40 minutes to afford the title compound (1.06 g) as a clear oil. LC-MS (ES) m/z=349 [M+H]+.

후처리

  1. temperatureheated at 100° C. overnight
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionredissolved with 150 mL of EtOAc
  4. washThe resulting organic mixture was washed with water (50 mL), brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting clear oil was purified in 50 g Biotage SNAP column with gradient of 0 to 50% of EtOAc in Hexane over 40 minutes

출처 및 근거

ORD 기록
ord-a86890251bd84838a54287aad230ff6c
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08697685B2

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