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

HRID 1257881Notes

Reaction equation

HRID 1257881 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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

Workup

  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%)

Sources & evidence

ORD record
ord-7e17d24f16ba453f8fcacf35a315121b
Source dataset
uspto-grants-2013_06
Patent number
US08461330B2

Reaction notes

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