Sulfuric Acid → Di-tert-butyl ether

HRID 1010487노트

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HRID 1010487 반응식
C(N1[CH2:13][C@@H:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:11][C@H](C(OC)=O)[C@H]1C(OCC1C=CC=CC=1)=O)C1C=CC=CC=1.[CH3:33]C(=C)C.C(N1C[C@@H](O)C[C@H](C(OC)=O)[C@H]1C(OCC1C=CC=CC=1)=O)C1C=CC=CC=1.S(=O)(=O)(O)O>>[C:15]([O:14][C:12]([CH3:11])([CH3:13])[CH3:33])([CH3:16])([CH3:17])[CH3:18]

참가 물질

5

반응물 4

HCID 1118Sulfuric AcidHCID 8255Isobutylene2회HCID 866214892-benzyl 3-methyl (2S,3S,5S)-1-benzyl-5-tert-butoxypiperidine-2,3-dicarboxylateHCID 866214902-benzyl 3-methyl(2S,3S,5S)-1-benzyl-5-hydroxypiperidine-2,3-dicarboxylate

생성물 1

HCID 22541Di-tert-butyl ether수율 51%

실험 절차

Part 1. 2-benzyl 3-methyl (2S,3S,5S)-1-benzyl-5-tert-butoxypiperidine-2,3-dicarboxylate: Isobutylene (2.96 mL, 0.0313 mol) was collected at −78 Celsius. To the cold isobutylene was added 2-benzyl 3-methyl (2S,3S,5S)-1-benzyl-5-hydroxypiperidine-2,3-dicarboxylate (0.60 g, 0.0016 mol) tetrahydrofuran (3.00 mL, 0.0370 mol), sulfuric acid (0.021 mL, 0.00039 mol). The reaction was sealed and allowed to warm up to rt and stirred at rt overnight. The mixture was cooled to −78 Celsius again. The seal was replaced with a septa connecting with a balloon. The reaction was then allowed to warm up to rt gradually to allow the evaporating of excess isobutylene. The residue was diluted with EtOAc, neutralized with aq. sodium hydroxide. The organic layers were washed with brine, dried. The residue was purified on silica gel, eluting with 0 to 30% EtOAc in hexane, to afford the tert-butyl ether (0.35 g, 51%). MS (ESI): (M+H)+=440.25.

후처리

  1. customThe reaction was sealed
  2. temperatureThe mixture was cooled to −78 Celsius again
  3. temperatureto warm up to rt gradually
  4. customevaporating of excess isobutylene
  5. additionThe residue was diluted with EtOAc
  6. washThe organic layers were washed with brine
  7. customdried
  8. customThe residue was purified on silica gel
  9. washeluting with 0 to 30% EtOAc in hexane

출처 및 근거

ORD 기록
ord-61ec91c9ea8c4d0fa9d0b521cb7c68e5
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07973041B2

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