N-BOC-ethylenediamine → Tert-butyl 2-(2-tert-butoxybenzylamino)ethylcarbamate

HRID 403120노트

반응식

HRID 403120 반응식
[C:1]([NH:8][CH2:9][CH2:10][NH2:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:12]([O:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH:19]=O)([CH3:15])([CH3:14])[CH3:13].[BH4-].[Na+]>CC#N>[C:12]([O:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH2:19][NH:11][CH2:10][CH2:9][NH:8][C:1](=[O:2])[O:3][C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:15])([CH3:13])[CH3:14]

참가 물질

5

반응물 3

HCID 187201N-BOC-ethylenediamineHCID 4311764Sodium borohydrideHCID 149555262-tert-Butoxybenzaldehyde

생성물 1

HCID 70896393Tert-butyl 2-(2-tert-butoxybenzylamino)ethylcarbamate수율 97%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

N-Boc-ethylenediamine (2.6 g, 16 mmol) and 8 (2.9 g, 16 mmol) were added to 250 mL of CH3CN and the reaction mixture was refluxed under argon for 4 hr. After cooling down to room temperature, the solvent was removed and the residue was redissolved in MeOH. The solvent was then evaporated and NaBH4 (3 g, 16 mmol) was added and stirred overnight. The solvent was evaporated, followed by extraction with CH2Cl2. The CH2Cl2 extract was concentrated and purified by a silica gel column using 2% methanolic NH3 (7 M NH3 in methanol/98% CH2Cl2 as eluent to yield the desired product as a pale yellow oil (97%). 1H NMR (CDCl3) δ 7.204 (dd, 1H, Ar), 7.115 (ddd, 1H, Ar), 7.007 (dd, 1H, Ar), 6.930 (ddd, 1H, Ar), 3.718 (s, 2H, —CH2—), 3.175 (d, 2H, —CH2—), 2.638 (t, 2H, —CH2—), 1.402 (s, 9H, —C(CH3)3), 1.382 (s, 9H, —C(CH3)3). Mass Spect.=323.23 (M+H)+.

후처리

  1. temperaturethe reaction mixture was refluxed under argon for 4 hr
  2. customthe solvent was removed
  3. dissolutionthe residue was redissolved in MeOH
  4. customThe solvent was then evaporated
  5. customThe solvent was evaporated
  6. extractionfollowed by extraction with CH2Cl2
  7. extractionThe CH2Cl2 extract
  8. concentrationwas concentrated
  9. custompurified by a silica gel column

출처 및 근거

ORD 기록
ord-914755edcedb48aeac79fd04f99ca8c6
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08747810B2

반응 노트

불러오는 중…