Proton sponge → Benzyl (1-(methoxymethyl)cyclopropyl)carbamate

HRID 1257879Notes

Reaction equation

HRID 1257879 reaction equation
[CH2:1]([O:8][C:9](=[O:16])[NH:10][C:11]1([CH2:14][OH:15])[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[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>[CH2:1]([O:8][C:9](=[O:16])[NH:10][C:11]1([CH2:14][O:15][CH3:17])[CH2:13][CH2:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 88675Proton spongeHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 22178711Benzyl (1-(hydroxymethyl)cyclopropyl)carbamate

Product 1

HCID 72942059Benzyl (1-(methoxymethyl)cyclopropyl)carbamateYield 42.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of benzyl[1-(hydroxymethyl)cyclopropyl]carbamate (0.32 g, 0.0014 mol) in methylene chloride (5.0 mL) was added sequentially powdered MS 4 Å, N,N,N′,N′-tetramethyl-1,8-naphthalenediamine (0.77 g, 0.0036 mol), and trimethyloxonium tetrafluoroborate (0.43 g, 0.0029 mol) at RT. The mixture was stirred for 5 h, filtered through a pad of Celite, and washed with EtOAc. The filtrate was washed with 1N HCl, 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 (140 mg, 41%). LCMS: (M+H)=236.1.

Workup

  1. filtrationfiltered through a pad of Celite
  2. washwashed with EtOAc
  3. washThe filtrate was washed with 1N HCl, 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-df0473224a994ceb8cbcf0d4f967d67d
Source dataset
uspto-grants-2013_06
Patent number
US08461330B2

Reaction notes

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