Water → HCID 44252106, compound

HRID 2063726Notes

Reaction equation

HRID 2063726 reaction equation
[BH4-].[Na+].[CH3:3][N:4]([CH3:28])[C:5]1([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[CH:21]=2)[CH2:10][CH2:9][CH:8]([C:11](=[O:19])[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:7][CH2:6]1.O>CO>[CH3:28][N:4]([CH3:3])[C:5]1([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[CH:21]=2)[CH2:10][CH2:9][CH:8]([CH:11]([OH:19])[CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydride2×HCID 66886881HCID 66886881, compound

Product 1

HCID 44252106HCID 44252106, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (24 mg, 0.6 mmol) was added to a solution of the product from stage 2 (112 mg, 0.3 mmol) in anhydrous methanol (5 ml) at 0° C. and the mixture was stirred at room temperature for 3 h. Further sodium borohydride (12 mg, 0.3 mmol) was then added and the mixture was stirred at room for a further 2 h. Water (20 ml) was added to the mixture. The solvent was removed i. vac. and the aqueous suspension was extracted with ethyl acetate (3×10 ml). The combined organic phases were dried with sodium sulfate and concentrated i. vac. The crude product (76 mg) was purified by flash chromatography (10 g, 20×1.1 cm) with methylene chloride/methanol [(95.5)+1% ammonia solution (30% in H2O)].

Workup

  1. stirringthe mixture was stirred at room for a further 2 h
  2. customThe solvent was removed i
  3. extractionand the aqueous suspension was extracted with ethyl acetate (3×10 ml)
  4. dry with materialThe combined organic phases were dried with sodium sulfate
  5. concentrationconcentrated i
  6. customThe crude product (76 mg) was purified by flash chromatography (10 g, 20×1.1 cm) with methylene chloride/methanol [(95.5)+1% ammonia solution (30% in H2O)]

Sources & evidence

ORD record
ord-ee8338b60469473da0fec8ac4d254142
Source dataset
uspto-grants-2012_10
Patent number
US08288406B2

Reaction notes

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