Sodium borohydride → HCID 90412642, compound

HRID 1746636Notes

Reaction equation

HRID 1746636 reaction equation
[I:1][C:2]1[C:3](=[O:33])[C@@H:4]2[O:8][C:7]([CH3:10])([CH3:9])[O:6][C@@H:5]2[C:11]=1[CH2:12][O:13][C:14]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[BH4-].[Na+]>CO>[I:1][C:2]1[C@H:3]([OH:33])[C@@H:4]2[O:8][C:7]([CH3:10])([CH3:9])[O:6][C@@H:5]2[C:11]=1[CH2:12][O:13][C:14]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 90412698HCID 90412698, compound

Product 1

HCID 90412642HCID 90412642, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of compound 6 (from Example 6b) was added to the reactor and cooled to 0° C. 2.2 kg MeOH was added followed by addition of CeCl3.7H2O (355 g) and the mixture stirred for 1 h to result homogeneous solution. NaBH4 (8.8 g) was added in portions at 0° C., stirred for 30 min, IPC showed the reaction started and additional NaBH4 (30 g) was added in portions with stirring for 1 h at 0° C. IPC showed complete consumption of compound 6. Saturated NH4Cl (0.27 kg) was added followed by celite (266 g) and the mixture stirred for 30 min after which it was filtered, washed with water (12 L×3), and dried over Na2SO4 to give compound 7 in MTBE solution (5.5 kg), which was concentrated (below 40° C.) to furnish a residue. DMF (3 kg) was added and the solution was used directly in the next step.

Workup

  1. customto result homogeneous solution
  2. stirringstirred for 30 min
  3. stirringwith stirring for 1 h at 0° C
  4. customconsumption of compound 6
  5. additionSaturated NH4Cl (0.27 kg) was added
  6. stirringthe mixture stirred for 30 min after which it
  7. filtrationwas filtered
  8. washwashed with water (12 L×3)
  9. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-38af2c3247b34f38aacc984f29d32e0a
Source dataset
uspto-grants-2015_10
Patent number
US09150520B2

Reaction notes

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