Acetic Acid → HCID 69316373, compound

HRID 2219668Notes

Reaction equation

HRID 2219668 reaction equation
[C:1]1(=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:8]([O:12][C:13]([NH:15][CH2:16][CH2:17][NH2:18])=[O:14])([CH3:11])([CH3:10])[CH3:9].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>O1CCCC1>[CH:1]1([NH:18][CH2:17][CH2:16][NH:15][C:13]([O:12][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:14])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 7967CyclohexanoneHCID 187201N-BOC-ethylenediamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 69316373HCID 69316373, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.04 mL (1.0 mmol) of cyclohexanone and 1.6 g (1.0 mmol) of N-(2-t-butoxycarbonylaminoeth-1-yl)amine in 24 mL of tetrahydrofuran were added 0.71 mL (1.2 mmol) of acetic acid and 2.97 g (1.4 mmol) of sodium triacetoxyborohydride. The reaction stirred at room temperature for 20 hr then saturated sodium bicarbonate (12 mL) was added and the mixture extracted with ethyl acetate (12 mL). The organic phase was washed with more saturated sodium bicarbonate (12 mL) and brine (12 mL). At this point a crystalline precipitate formed which was filtered off and washed with water and ethyl acetate to leave the title compound.

Workup

  1. extractionthe mixture extracted with ethyl acetate (12 mL)
  2. washThe organic phase was washed with more saturated sodium bicarbonate (12 mL) and brine (12 mL)
  3. customAt this point a crystalline precipitate formed which
  4. filtrationwas filtered off
  5. washwashed with water and ethyl acetate

Sources & evidence

ORD record
ord-8a25027da996400fbcdf3859d7c3c830
Source dataset
uspto-grants-2008_08
Patent number
US07414067B2

Reaction notes

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