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

HRID 500223Notes

Reaction equation

HRID 500223 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 4A, 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-eab2da80033d4ec68dff9106959fe5f5
Source dataset
uspto-grants-2010_08
Patent number
US07767675B2

Reaction notes

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