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

HRID 749085Notes

Reaction equation

HRID 749085 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) δ 7.35 (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-1882d7fe05fc467b85de2ac0c8c9dc93
Source dataset
uspto-grants-2008_07
Patent number
US07402586B2

Reaction notes

Loading…