Sodium borohydride → HCID 178476301, compound

HRID 1404405Notes

Reaction equation

HRID 1404405 reaction equation
C(O)CO.C(=O)=O.[C:8]([O:11][CH2:12][CH2:13][C@H:14]1[CH2:19][CH2:18][C@H:17]([CH:20]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH:22]=[O:23])[CH2:16][CH2:15]1)(=[O:10])[CH3:9].[BH4-].[Na+]>C(O)C>[C:8]([O:11][CH2:12][CH2:13][C@H:14]1[CH2:19][CH2:18][C@H:17]([CH:20]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:22][OH:23])[CH2:16][CH2:15]1)(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 86601574Dry ice ethyleneglycolHCID 178476300HCID 178476300, compound

Product 1

HCID 178476301HCID 178476301, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (ethylene glycol+dry ice) solution of 2-(trans-4-(1-(tert-butoxycarbonylamino)-3-oxopropyl)cyclohexyl)ethyl acetate (1.88 g, 5.5 mmol) in ethanol (90 mL) was added NaBH4 (0.212 g, 5.5 mmol). The mixture was stirred at −10˜15° C. for 10 min and 0° C. for 10 min, and then quenched by addition of saturated aqueous NH4Cl solution (30 mL) and brine (30 mL). After removal of the volatile by evaporation, the aqueous residue was extracted with EtOAc, dried over Na2SO4. Purification by flash column chromatography (eluent: 30% EtOAc in hexanes to 40%) gave the alcohol product (1.0 g, 53%). LC/MC: 366.1 (MNa)+.

Workup

  1. customquenched by addition of saturated aqueous NH4Cl solution (30 mL) and brine (30 mL)
  2. customAfter removal of the
  3. customvolatile by evaporation
  4. extractionthe aqueous residue was extracted with EtOAc
  5. dry with materialdried over Na2SO4
  6. customPurification by flash column chromatography (eluent: 30% EtOAc in hexanes to 40%)

Sources & evidence

ORD record
ord-620245cc90004280a4d74ebc9deba5ce
Source dataset
uspto-grants-2014_12
Patent number
US08912169B2

Reaction notes

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