Potassium Carbonate → Benzyl (1-(hydroxymethyl)cyclopropyl)carbamate

HRID 1067018Notes

Reaction equation

HRID 1067018 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1([C:15](O)=[O:16])[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H]1[BH2][H][BH2]1.C([O-])([O-])=O.[K+].[K+]>O1CCCC1>[CH2:1]([O:8][C:9]([NH:11][C:12]1([CH2:15][OH:16])[CH2:13][CH2:14]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 35890121-{[(Benzyloxy)carbonyl]amino}cyclopropane-1-carboxylic acid

Product 1

HCID 22178711Benzyl (1-(hydroxymethyl)cyclopropyl)carbamateYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-(benzyloxycarbonylamino)cyclopropanecarboxylic acid (500 mg, 2.1 mmol) in tetrahydrofuran (5 mL) at 0° C. was added B2H6. THF (1M, 2.1 mL, 2.1 mmol). The mixture was stirred at ambient temperature overnight, treated with K2CO3 (1.0 g in 5 mL H2O) and extracted with methylene chloride (3×10 mL). The organic layer was washed with brine (10 mL) and dried over Na2SO4. After evaporating the solvent, the residue was by chromatography (1:1 ethyl acetate:hexane) to give the title compound as a white solid (200 mg, 43%). 1H-NMR (300 MHz, CDCl3) δ7.35 (m, 5H), 5.30 (br s, 1H), 5.10 (s, 2H), 3.61 (s, 2H), 3.02 (br s, 1H), 0.86 (s, 4H).

Workup

  1. extractionextracted with methylene chloride (3×10 mL)
  2. washThe organic layer was washed with brine (10 mL)
  3. dry with materialdried over Na2SO4
  4. customAfter evaporating the solvent

Sources & evidence

ORD record
ord-1656ec16778446efa5fba5c7e7473ed0
Source dataset
uspto-grants-2001_06
Patent number
US06245763B1

Reaction notes

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