Hydrochloric Acid → HCID 21955378, compound

HRID 2213040Notes

Reaction equation

HRID 2213040 reaction equation
[BH4-].[Li+].[OH:3][CH2:4][CH2:5][CH2:6][C:7]1([C:20](OCC2C=CC=CC=2)=[O:21])[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1.Cl.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.C1(C)C=CC=CC=1>[OH:21][CH2:20][C:7]1([CH2:6][CH2:5][CH2:4][OH:3])[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 4148881Lithium borohydrideHCID 69559203HCID 69559203, compound

Product 1

HCID 21955378HCID 21955378, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 22635083Tetrahydrofuran tolueneSolvent

Conditions

Temperature
60 °C

Procedure

Lithium borohydride (500 mg, 22.7 mmol) was added to a solution of 1-(1,1-dimethylethyl) 4-phenylmethyl 4-(3-hydroxypropyl)-1,4-piperidinedicarboxylate (Description 136, 1.05 g, 2.79 mmol) in tetrahydrofuran/toluene (50:50, 20 mL). and the mixture was stirred at 60° C. for 4 hours. The mixture was cooled and hydrochloric acid (2M, 10 mL) was added. The mixture was poured into aqueous sodium carbonate (10%, 100 mL) and extracted with ethyl acetate (3×50 mL). The combined organic fractions were dried (Na2SO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with EtOAc/MeOH (100:0 increasing to 95:5) to give the title compound (563 mg, 74%). 1H NMR (400 MHz, CDCl3) δ 3.67 (2H, t, J 7 Hz), 3.48 (2H, s), 3.47–3.40 (2H, m), 3.35–3.25 (2H, m), 1.7 (2H, br s), 1.6–1.3 (8H, m), and 1.44 (9H, s).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. dry with materialThe combined organic fractions were dried (Na2SO4)
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by flash column chromatography on silica gel
  6. washeluting with EtOAc/MeOH (100:0 increasing to 95:5)

Sources & evidence

ORD record
ord-0d1505ab055046c289016d2437e9cf33
Source dataset
uspto-grants-2006_09
Patent number
US07105507B2

Reaction notes

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