Sodium borohydride → 1-(hydroxymethyl)-N-propylcyclopropanecarboxamide

HRID 471662Notes

Reaction equation

HRID 471662 reaction equation
[CH2:1]([NH:4][C:5]([C:7]1([C:10](OCC)=[O:11])[CH2:9][CH2:8]1)=[O:6])[CH2:2][CH3:3].[BH4-].[Na+]>CCO>[OH:11][CH2:10][C:7]1([C:5]([NH:4][CH2:1][CH2:2][CH3:3])=[O:6])[CH2:8][CH2:9]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 66746001Ethyl 1-(propylcarbamoyl)cyclopropanecarboxylate

Product 1

HCID 667460451-(hydroxymethyl)-N-propylcyclopropanecarboxamideYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 1-(propylcarbamoyl)cyclopropanecarboxylate (Example 198d) (1.65 g, 8.27 mmol) in EtOH (70 mL) was added NaBH4 (0.97 g, 25.64 mmol) at rt. The obtained mixture was stirred at rt over 2 days, quenched with 1.5M HCl and concentrated under reduced pressure. The concentrated mixture was extracted with EtOAc (4×70 mL), the combined extract was washed with saturated NaHCO3 and brine, and was dried over MgSO4. The filtrate was evaporated and the residue was purified by chromatography on silica gel using the solvent gradient hexanes→hexanes/EtOAc (1:9), to furnish 1.14 g (88%) of the product as a white solid. 1H-NMR (400 MHz, DMSO-d6) δ 7.49 (broad s, 1H), 5.09 (broad s, 1H), 3.49 (s, 2H), 3.05 (q, J=6.4 Hz, 2H), 1.41 (hex, J=7.6 Hz, 2H), 0.86-0.91 (m, 2H), 0.83 (t, J=7.2 Hz, 3H), 0.55-0.60 (m, 2H).

Workup

  1. customquenched with 1.5M HCl
  2. concentrationconcentrated under reduced pressure
  3. extractionThe concentrated mixture was extracted with EtOAc (4×70 mL)
  4. extractionthe combined extract
  5. washwas washed with saturated NaHCO3 and brine
  6. dry with materialwas dried over MgSO4
  7. customThe filtrate was evaporated
  8. customthe residue was purified by chromatography on silica gel using the solvent gradient hexanes→hexanes/EtOAc (1:9)

Sources & evidence

ORD record
ord-56ac5e1b62d94f6b89a594ebe9c94152
Source dataset
uspto-grants-2014_01
Patent number
US08633186B2

Reaction notes

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