Triethylamine → HCID 178515017, compound

HRID 449361

Reaction equation

HRID 449361 reaction equation
Cl.[NH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([OH:9])[CH2:5][CH2:4]1.C(N1[C:19](=[O:20])[C:18]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:17]2[C:16]1=[O:25])(OCC)=O.C(N(CC)CC)C>C(Cl)Cl.O>[OH:9][C@H:6]1[CH2:7][CH2:8][C@H:3]([N:2]2[C:19](=[O:20])[C:18]3[C:17](=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:16]2=[O:25])[CH2:4][CH2:5]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31187N-CarbethoxyphthalimideHCID 178479278HCID 178479278, compound

Product 1

HCID 178515017HCID 178515017, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of trans-4-aminocyclohexanol hydrochloride (1.0 g, 6.6 mmol) (Aldrich, Cat. #263761), N-carbethoxyphthalimide (1.4 g, 6.6 mmol) (Aldrich, Cat. #C5459), and triethylamine (2.0 mL, 14 mmol) in methylene chloride (10 mL) was stirred at r.t. overnight. The mixture was diluted with water, and extracted with ethyl acetate (3×20 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes to afford the desired product (1.2 g, 76%).

Workup

  1. extractionextracted with ethyl acetate (3×20 mL)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes

Sources & evidence

ORD record
ord-13f3dec127c3446690ea84dccfa832ff
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Linked notes

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