Sodium triacetoxyborohydride → HCID 58504055, compound

HRID 2407788Notes

Reaction equation

HRID 2407788 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:24])[CH2:9][CH2:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1.O=[CH:26][CH2:27][CH2:28][NH:29][C:30](=[O:39])[O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(OCC)(=O)C>[CH2:32]([O:31][C:30]([NH:29][CH2:28][CH2:27][CH2:26][NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:24])[CH2:9][CH2:10][CH:11]1[CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[CH2:15][CH2:16]1)=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 10398106Benzyl (3-Oxopropyl)carbamateHCID 58504081HCID 58504081, compound

Product 1

HCID 58504055HCID 58504055, compoundYield 87.8%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound prepared in Example 302 (0.455 g) was suspended in 1,2-dichloroethane (10 mL). Benzyl 3-oxopropylcarbamate (0.425 g) and beaded molecular sieves were added and the reaction mixture stirred at room temperature for 1 hour. Sodium triacetoxyborohydride (0.870 g) was added and the reaction mixture stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate, washed with saturated aqueous sodium bicarbonate solution and brine. The organics were dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford the crude material, which was purified by flash column chromatography (eluant: 20-30% ethyl acetate/hexane) to furnish the title compound (0.629 g) with the following physical properties.

Workup

  1. additionwere added
  2. stirringthe reaction mixture stirred at room temperature overnight
  3. washwashed with saturated aqueous sodium bicarbonate solution and brine
  4. dry with materialThe organics were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto afford the crude material, which
  8. customwas purified by flash column chromatography (eluant: 20-30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-debe572ce94e4d25817d5a2c75685a3b
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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