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

HRID 48886Notes

Reaction equation

HRID 48886 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-6c8c10fc635f4daaba1d98e52f040907
Source dataset
uspto-grants-2004_03
Patent number
US06706021B2

Reaction notes

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