Sodium borohydride → HCID 21069248, compound

HRID 1244174Notes

Reaction equation

HRID 1244174 reaction equation
[C:1]([O:5][C:6]([C:8]1([S:14]([N:17]2[CH2:22][CH2:21][CH:20]([CH2:23][CH:24]=[O:25])[CH2:19][CH2:18]2)(=[O:16])=[O:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[C:1]([O:5][C:6]([C:8]1([S:14]([N:17]2[CH2:18][CH2:19][CH:20]([CH2:23][CH2:24][OH:25])[CH2:21][CH2:22]2)(=[O:16])=[O:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21069249HCID 21069249, compound

Product 1

HCID 21069248HCID 21069248, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The aldehyde from Example A6 (1.43 g, 3.81 mmol) in MeOH (15 mL) at 0° C. was treated with NaBH4 (144 mg, 3.81 mmol) in portions. Upon completion of addition, the ice bath was removed, and the mixture was stirred at room temperature for 2 hr. The reaction was then quenched with saturated NH4Cl (˜5 mL). After adding water (15 mL), the mixture was extracted with methylene chloride (3×30 mL). The organics were dried (magnesium sulfate). Concentration in vacuo afforded the alcohol as an oil (1.44 g, quantitative conversion). NMR(CDCl3) δ 1.28 (dt, 2H), 1.33–1.42 (m, 2H), 1.47–1.65 (m, 10H), 1.70 (d, 2H), 2.10 (dt, 2H), 2.32 (d, 2H), 2.94 (dt, 2H), 3.30 (dt, 2H), 3.68 (t, 2H), 3.76 (d, 2H), 3.96 (dd, 2H).

Workup

  1. additionUpon completion of addition
  2. customthe ice bath was removed
  3. customThe reaction was then quenched with saturated NH4Cl (˜5 mL)
  4. additionAfter adding water (15 mL)
  5. extractionthe mixture was extracted with methylene chloride (3×30 mL)
  6. dry with materialThe organics were dried (magnesium sulfate)
  7. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-511eafcd71bb48d1b9e502d24990723d
Source dataset
uspto-grants-2006_10
Patent number
US07119203B2

Reaction notes

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