Hydrochloric Acid → HCID 13543373, compound

HRID 1048857Notes

Reaction equation

HRID 1048857 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[CH2:12][O:11][CH2:10][CH:9]1[C:15](O)=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[BH4-].[Na+].Cl>C1COCC1.C(OC(Cl)=O)C.O>[CH2:1]([N:8]1[CH:9]([CH2:15][OH:16])[CH2:10][O:11][CH2:12][C:13]1=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 4311764Sodium borohydrideHCID 13543370HCID 13543370, compound

Product 1

HCID 13543373HCID 13543373, compoundYield 40.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 10928Ethyl chloroformateSolvent

Procedure

To a stirred solution of 4-benzyl-5-oxomorpholine-3-carboxylic acid (450 mg, 1.91 mmole) and triethylamine (0.28 mL, 2.5 mmole) in THF, ethylchloroformate (0.2 mL) was added dropwise for 20 min at −10° C. The reaction mixture was stirred for additional 30 min and filtered. The filtrate was added for 30 min to a solution of NaBH4 (200 mg, 5.28 mmole) in water (15 mL) at 0° C. The reaction mixture was stirred for 4 h at 10° C. and acidified with 2M HCl. THF was evaporated under reduced pressure and the aqueous residue extracted into DCM, washed with saturated NaHCO3 (20 mL), dried over Na2SO4, concentrated and purified by flash chromatography using eluent 5% MeOH in DCM to get the title compound (170 mg) as oily mass, m/z 222.

Workup

  1. filtrationfiltered
  2. stirringThe reaction mixture was stirred for 4 h at 10° C.
  3. customTHF was evaporated under reduced pressure
  4. extractionthe aqueous residue extracted into DCM
  5. washwashed with saturated NaHCO3 (20 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. custompurified by flash chromatography

Sources & evidence

ORD record
ord-8e8dce59fd514ec19db799e091855e4a
Source dataset
uspto-grants-2016_07
Patent number
US09382216B2

Reaction notes

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