Sodium triacetoxyborohydride → HCID 178522354, compound

HRID 469706Notes

Reaction equation

HRID 469706 reaction equation
[O:1]=[C:2]1[C:8]([NH:9][C:10](=[O:18])[C:11]2[CH:16]=[CH:15][CH:14]=[N:13][C:12]=2[OH:17])=[CH:7][C:6](=[O:19])[CH:5]2[CH:3]1[O:4]2.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[OH:17][C:12]1[N:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:10]([NH:9][C:8]1[CH:2]([OH:1])[CH:3]2[CH:5]([C:6](=[O:19])[CH:7]=1)[O:4]2)=[O:18]

Participants

4

Reactant 2

HCID 5049666Sodium triacetoxyborohydrideHCID 178522353HCID 178522353, compound

Product 1

HCID 178522354HCID 178522354, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of compound 7a (30 mg, 0.092 mmol, 80% purity) in methanol (4 mL) cooled to 0° C. under an inert nitrogen atmosphere was added sodium triacetoxyborohydride (30 mg, 0.142 mmol) in one portion. The solution was stirred at this temperature for 15 minutes before bringing to room temperature. After stirring an additional 45 minutes, the reaction was judged complete by TLC. The methanol was evaporated to approx. 2 mL volume and the flask was cooled in an ice bath for 10 minutes. The precipitate was then filtered and rinsed with methanol (2×3 mL). After drying under high vacuum, 10 mg (42% yield) of compound 8a as a pale yellow solid was isolated. The purity was 95% by HPLC (Restek Pinnacle II column, C18, 5μ, 250×4.6 mm; mobile phase: 5 minutes at 5% acetonitrile in water, then 5 to 100% acetonitrile in water over 20 min.; flow rate: 1.5 mL/min; detector: 316 nm (VWD). The product structure was confirmed by 1H NMR. NMR (DMSO-d6): δ12.70 (br.s, 1H), 12.50 (br.s, 1H), 8.35 (m, 1H), 7.85 (m, 1H), 6.90 (m, 1H), 6.55 (m, 2H), 4.80 (m, 1H), 3.80 (m, 1H), 3.40 (m, 1H) ppm.

Workup

  1. custombefore bringing to room temperature
  2. stirringAfter stirring an additional 45 minutes
  3. customThe methanol was evaporated to approx. 2 mL volume
  4. temperaturethe flask was cooled in an ice bath for 10 minutes
  5. filtrationThe precipitate was then filtered
  6. washrinsed with methanol (2×3 mL)
  7. customAfter drying under high vacuum

Sources & evidence

ORD record
ord-6fea5afeade8420681187779df3188d2
Source dataset
uspto-grants-2014_01
Patent number
US08629164B2

Reaction notes

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