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

HRID 500225ノート

反応式

HRID 500225 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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 4A, 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

後処理

  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%)

出典と根拠

ORDレコード
ord-1f72c409940d4e55b49b25fdeaefeebe
出典データセット
uspto-grants-2010_08
特許番号
US07767675B2

反応ノート

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