Binap, (A+-)- → tert-butyl {6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}(pentyloxy)carbamate

HRID 1258571노트

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HRID 1258571 반응식
Br[C:2]1[N:7]=[C:6]([CH2:8][O:9][N:10]=[C:11]([C:18]2[N:22]([CH3:23])[N:21]=[N:20][N:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:5]=[CH:4][CH:3]=1.[C:24]([O:28][C:29](=[O:37])[NH:30][O:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])([CH3:27])([CH3:26])[CH3:25].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C(O[K])(C)(C)C>C1(C)C=CC=CC=1>[CH3:23][N:22]1[C:18]([C:11](=[N:10][O:9][CH2:8][C:6]2[N:7]=[C:2]([N:30]([O:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[C:29](=[O:37])[O:28][C:24]([CH3:25])([CH3:26])[CH3:27])[CH:3]=[CH:4][CH:5]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:19][N:20]=[N:21]1

참가 물질

6

반응물 4

HCID 634876Binap, (A+-)-HCID 86653112N-[(6-bromopyridin-2-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimineHCID 86653126Tert-butyl (pentyloxy)carbamateHCID 178418922HCID 178418922, 화합물

생성물 1

HCID 86653127tert-butyl {6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}(pentyloxy)carbamate수율 43.3%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
90 °C

실험 절차

In a purged and dried vessel, N-[(6-bromopyridin-2-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (0.2 g, 0.536 mmol, 1 eq.) was dissolved in 3 ml of toluene and tert-butyl(pentyloxy)carbamate (0.217 g, 1.072 mmol 2 eq.) was added followed by Pddba2 (0.065 g, 0.113 mmol, 0.21 eq.) and BINAP (0.069 g, 0.113 mmol, 0.21 eq.). Then tBuOK (0.12 g, 1.07 mmol, 2 eq.) was added and the vessel purged with argon and sealed. The reaction was stirred at 90° C. for 24 h. The solvent was evaporated and residue taken in EtOAc, filtered through “celite”, washed with H2O, dried over MgSO4, and concentrated. The crude was purified by chromatography on silica gel to give tert-butyl {6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}(pentyloxy)carbamate (0.115 g, 41%) as a viscous yellow oil.

후처리

  1. customIn a purged
  2. customdried vessel
  3. customthe vessel purged with argon
  4. customsealed
  5. customThe solvent was evaporated
  6. filtrationfiltered through “celite”
  7. washwashed with H2O
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated
  10. customThe crude was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-ea1197370c7946a39f5806971d8c2027
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08466176B2

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