Acetic Acid → HCID 59030589, compound

HRID 1619200Notes

Reaction equation

HRID 1619200 reaction equation
[OH:1][CH2:2][C:3]1([C:10]2[N:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1.[CH:16]1([NH2:19])[CH2:18][CH2:17]1.C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[OH-].[Na+]>C(#N)C>[CH:16]1([NH:19][CH:6]2[CH2:7][CH2:8][C:3]([CH2:2][OH:1])([C:10]3[N:15]=[CH:14][CH:13]=[CH:12][N:11]=3)[CH2:4][CH2:5]2)[CH2:18][CH2:17]1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 69828CyclopropylamineHCID 5049666Sodium triacetoxyborohydrideHCID 59030615HCID 59030615, compound

Product 1

HCID 59030589HCID 59030589, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 4-(hydroxymethyl)-4-(pyrimidin-2-yl)cyclohexanone (238 mg, 1.15 μmol), cyclopropylamine (106 μl, 1.50 mmol), and acetic acid (87 μl, 1.50 mmol) in acetonitrile (6 mL) was treated at 0° C. with NaBH(OAc)3 (367 mg, 1.73 mmol). After being stirred at 25° C. for 20 h, the reaction was then basified (1 M aqueous NaOH, pH˜12), extracted (5×10% MeOH/DCM), and washed (1× brine). The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure to provide (4-(cyclopropylamino)-1-(pyrimidin-2-yl)cyclohexyl)methanol (281 mg, 1.14 mmol, quantitatively) as a pale yellow film.

Workup

  1. extractionextracted (5×10% MeOH/DCM)
  2. washwashed (1× brine)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7c2557a2f9fb4b9b9d699c6b409a703c
Source dataset
uspto-grants-2014_07
Patent number
US08772296B2

Reaction notes

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