Acetic Acid → 4-(Spiro[5.5]undec-3-ylaminomethyl)benzoic acid methyl ester

HRID 1633985Notes

Reaction equation

HRID 1633985 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][NH2:12])=[CH:7][CH:6]=1.C(=O)([O-])[O-].[K+].[K+].C(O)(=O)C.[CH2:24]1[C:29]2([CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)[CH2:28][CH2:27][C:26](=O)[CH2:25]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.O>[CH3:2][O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][NH:12][CH:32]2[CH2:33][CH2:34][C:29]3([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]3)[CH2:30][CH2:31]2)=[CH:7][CH:6]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 11430Potassium Carbonate2×HCID 574172Spiro[5.5]undecan-3-oneHCID 2729253Methyl 4-(aminomethyl)benzoate hydrochlorideHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 235501414-(Spiro[5.5]undec-3-ylaminomethyl)benzoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

4-Aminomethylbenzoic acid methyl ester hydrochloride (1.45 g, 7.2 mmol) was suspended in 1,2-dichloroethane (50 mL) and added saturated aqueous potassium carbonate. The phases were separated and the aqueous layer was extracted with another portion of 1,2-dichloro-ethane (50 mL). The combined organic phases were added glacial acetic acid (435 μL, 7.6 mmol) followed by spiro[5.5]undecan-3-one (1.2 g, 7.2 mmol). The suspension was stirred for 30 min at 25° C. and sodium triacetoxyborohydride (2.27 g, 10.7 μmol) was added. After stirring for 2 days at 25° C., water (100 mL) and saturated aqueous potassium carbonate (15 mL) were added. The phases were separated and the aqueous layer was extracted with 1,2-di-chloroethane (2×100 mL). The combined organic phases were washed with water (100 mL) and brine (100 mL), dried over MgSO4 and evaporated to afford 4-(spiro[5.5]undec-3-ylaminomethyl)benzoic acid methyl ester which was used in the subsequent steps without further purification.

Workup

  1. customThe phases were separated
  2. extractionthe aqueous layer was extracted with another portion of 1,2-dichloro-ethane (50 mL)
  3. stirringAfter stirring for 2 days at 25° C.
  4. customThe phases were separated
  5. extractionthe aqueous layer was extracted with 1,2-di-chloroethane (2×100 mL)
  6. washThe combined organic phases were washed with water (100 mL) and brine (100 mL)
  7. dry with materialdried over MgSO4
  8. customevaporated

Sources & evidence

ORD record
ord-f5f891da2258402db015d59cb29a37be
Source dataset
uspto-grants-2003_01
Patent number
US06503949B1

Reaction notes

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