Sodium borohydride → HCID 20740331, compound

HRID 1883132Notes

Reaction equation

HRID 1883132 reaction equation
[BH4-].[Na+].[CH2:3]([O:5][C:6]([C:8]1[CH2:13][CH2:12][CH:11]([CH3:14])[CH2:10][C:9]=1[NH:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:7])[CH3:4]>C(O)(=O)C(C)C>[CH2:3]([O:5][C:6]([CH:8]1[CH2:13][CH2:12][CH:11]([CH3:14])[CH2:10][CH:9]1[NH:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:7])[CH3:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 20740332HCID 20740332, compound

Product 1

HCID 20740331HCID 20740331, compound

Reagents, catalysts & solvents 1

HCID 6590Isobutyric AcidSolvent

Conditions

Temperature
15 °C

Procedure

In a separate flask, sodium borohydride (3.8 g) was added in portions to isobutyric acid (60 mL) cooled to about 15° C. under nitrogen. After 15 minutes, the reaction was cooled to 0° C. and the above reaction solution containing 2-benzylamino-4-methyl-cyclohex-1-enecarboxylic acid ethyl ester was added dropwise. After stirring for 2 hours, the reaction was carefully quenched with 40 mL of 3 M aqueous hydrochloric acid. The organic layer was separated, and the aqueous layer washed with 50% ethyl acetate/hexanes. After making the aqueous layer basic with 2M sodium hydroxide, extraction with four portions of ethyl acetate was conducted. The organic layer was concentrated to about 50 mL, cooled to 0° C., and made acidic with 30% HBr in propionic acid. After 1 hour, a solid was collected (1.1 g). The mother liquor was made basic and extracted with ethyl acetate. After concentration, the residue was subjected to flash chromatography using hexanes/ethyl acetate to afford 1.31 g of 2-benzylamino-4-methyl-cyclohexanecarboxylic acid ethyl ester.

Workup

  1. temperaturethe reaction was cooled to 0° C.
  2. additionwas added dropwise
  3. customthe reaction was carefully quenched with 40 mL of 3 M aqueous hydrochloric acid
  4. customThe organic layer was separated
  5. washthe aqueous layer washed with 50% ethyl acetate/hexanes
  6. extractionbasic with 2M sodium hydroxide, extraction with four portions of ethyl acetate
  7. concentrationThe organic layer was concentrated to about 50 mL
  8. temperaturecooled to 0° C.
  9. waitAfter 1 hour
  10. customa solid was collected (1.1 g)
  11. extractionextracted with ethyl acetate
  12. concentrationAfter concentration

Sources & evidence

ORD record
ord-0ef725dc20494caca2e9de34f359030b
Source dataset
uspto-grants-2004_07
Patent number
US06759428B2

Reaction notes

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