Acetic Acid → HCID 69431261, compound

HRID 916904Notes

Reaction equation

HRID 916904 reaction equation
C(O[BH-](O[C:11](=[O:13])[CH3:12])OC(=O)C)(=O)C.[Na+].[CH:15]1([C:18](=O)[CH2:19]O)[CH2:17][CH2:16]1.C([NH2:29])C1C=CC=CC=1.[C:30](O)(=O)[CH3:31].[CH2:34]1[CH2:38]OC[CH2:35]1>>[NH2:29][C:30]1[CH:31]=[CH:16][CH:17]=[CH:15][C:18]=1[CH2:19][CH:11]([OH:13])[CH2:12][CH:35]1[CH2:34][CH2:38]1

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 7504BenzylamineHCID 8028TetrahydrofuranHCID 5049666Sodium triacetoxyborohydrideHCID 20361677HCID 20361677, compound

Product 1

HCID 69431261HCID 69431261, compound

Procedure

Sodium triacetoxyborohydride (51 g) was added to a solution of 1-cyclopropyl-2-hydroxyethanone (16.0 g), benzylamine (17.5 ml) and acetic acid (9.15 ml) in THF (300 ml) keeping the temperature at 25-30° C. After stirring for 24 hours the mixture was evaporated, treated with saturated sodium bicarbonate (250 ml) and extracted with ethyl acetate (10×200 ml). The combined organic extracts were dried (sodium sulphate) and evaporated. The residual oil gained was purified by flash chromatography (Silica, Merck 9385), eluting with DCM:ethanol:ammonia (967:30:3 to 945:50:5) to give 2-aminobenzyl-2-cyclopropylethanol (10.63 g).

Workup

  1. customat 25-30° C
  2. customwas evaporated
  3. additiontreated with saturated sodium bicarbonate (250 ml)
  4. extractionextracted with ethyl acetate (10×200 ml)
  5. dry with materialThe combined organic extracts were dried (sodium sulphate)
  6. customevaporated
  7. customThe residual oil gained was purified by flash chromatography (Silica, Merck 9385)
  8. washeluting with DCM:ethanol:ammonia (967:30:3 to 945:50:5)

Sources & evidence

ORD record
ord-210265c3eb864e61b92274b4360501b2
Source dataset
uspto-grants-2007_09
Patent number
US07271289B2

Reaction notes

Loading…