Sodium borohydride → HCID 44546739, compound

HRID 1967426Notes

Reaction equation

HRID 1967426 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:22]=[CH:23][CH:24]=1)[CH2:6][N:7]([CH3:21])[CH2:8][C:9]([C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=1)=[O:10].[BH4-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:22]=[CH:23][CH:24]=1)[CH2:6][N:7]([CH3:21])[CH2:8][CH:9]([C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=1)[OH:10]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 44546737HCID 44546737, compound

Product 1

HCID 44546739HCID 44546739, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
12.5 °C

Procedure

A solution of the ketone, Compound 4, (512.2 g, 1.57 mol) in methanol (4.0 L) was split equally into two flasks. To each half of the ice-cold solution was added sodium borohydride (33.0 g, 0.87 mol) in batches (˜30 min). After the addition, the reaction solution was stirred at 0° C. (internal temperature 10-15° C.) for 50 min before it was quenched slowly with water (˜500 mL). The reaction mixture was then concentrated in vacuo to remove most of the organic solvent. The residue obtained from the two batches were combined, extracted with dichloromethane (2×), dried over sodium sulfate and concentrated in vacuo. The alcohol, Compound 5, was obtained as a yellow oil (510.4 g, quantitative), and was used in the next step without further purification: 1H NMR (500 MHz, CDCl3) δ 7.84-7.80 (m, 4H), 7.47-7.44 (m, 3H), 7.27-7.24 (m, 1H), 6.92-6.83 (m, 3H), 4.92 (dd, J=10.0, 4.0 Hz, 1H), 4.14 (br s, 1H), 3.81 (s, 3H), 3.74 (d, J=13.0 Hz, 1H), 3.53 (d, J=13.0 Hz, 1H), 2.68-2.60 (m, 2H), 2.36 (s, 3H); ESI MS m/z 322 [M+H]+.

Workup

  1. additionAfter the addition
  2. customwas quenched slowly with water (˜500 mL)
  3. concentrationThe reaction mixture was then concentrated in vacuo
  4. customto remove most of the organic solvent
  5. customThe residue obtained from the two batches
  6. extractionextracted with dichloromethane (2×)
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-528deea92ba24f8a96247c411483233b
Source dataset
uspto-grants-2013_04
Patent number
US08420811B2

Reaction notes

Loading…