Proton sponge → tert-butyl[4-(methoxymethyl)tetrahydro-2H-pyran-4-yl]carbamate

HRID 1257881노트

반응식

HRID 1257881 반응식
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1([CH2:14][OH:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:17]N(C)C1C2C(=CC=CC=2N(C)C)C=CC=1.F[B-](F)(F)F.C[O+](C)C>C(Cl)Cl>[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1([CH2:14][O:15][CH3:17])[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 88675Proton spongeHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 67114425tert-butyl N-[4-(hydroxymethyl)oxan-4-yl]carbamate

생성물 1

HCID 90902949tert-butyl[4-(methoxymethyl)tetrahydro-2H-pyran-4-yl]carbamate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of tert-butyl[4-(hydroxymethyl)tetrahydro-2H-pyran-4-yl]carbamate (0.89 g, 3.8 mmol) in methylene chloride (19.2 mL) was added sequentially powdered MS 4 Å, N,N,N′,N′-tetramethyl-1,8-naphthalenediamine (2.0 g, 9.6 mmol), and trimethyloxonium tetrafluoroborate (1.1 g, 7.7 mmol) at RT. The mixture was stirred for 5 h., filtered through a pad of Celite, and washed with EtOAc. The filtrate was washed with aqueous CuSO4, water, brine, dried over MgSO4, filtered, and concentrated. The residue was purified by chromatography on silica gel with EtOAc in hexanes (0-30%) to afford the desired product. LCMS: (M+Na)=268.0

후처리

  1. filtrationfiltered through a pad of Celite
  2. washwashed with EtOAc
  3. washThe filtrate was washed with aqueous CuSO4, water, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel with EtOAc in hexanes (0-30%)

출처 및 근거

ORD 기록
ord-7e17d24f16ba453f8fcacf35a315121b
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461330B2

반응 노트

불러오는 중…