Sodium borohydride → HCID 57595182, compound

HRID 1785402Notes

Reaction equation

HRID 1785402 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[C:14]([CH:16]4[O:20][CH2:19][N:18]([CH3:21])[CH2:17]4)[CH:13]=[CH:12][N:11]3[C:22]=2[C:23]2[CH:28]=[CH:27][N:26]=[C:25]([S:29][CH3:30])[N:24]=2)=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[C:14]([CH:16]([OH:20])[CH2:17][N:18]([CH3:21])[CH3:19])[CH:13]=[CH:12][N:11]3[C:22]=2[C:23]2[CH:28]=[CH:27][N:26]=[C:25]([S:29][CH3:30])[N:24]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57595175HCID 57595175, compound

Product 1

HCID 57595182HCID 57595182, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 100 mL round bottom flask was charged with oxazolidine 41 (1.65 g, 3.91 mmol), ethanol (50 mL), and sodium borohydride (450 mg, 11.9 mmol), and stirred at room temperature for 3 hours. The reaction was then quenched with 16 mL of a 20% NH4Cl aqueous solution and concentrated under reduced pressure, then diluted with water and neutralized with an aqueous solution of potassium carbonate. The solution was then extracted with methylene chloride (3×50 mL). The organic extracts were then pooled, dried over MgSO4, filtered and concentrated under reduced pressure to give (dimethylamino)ethanol 42 (crude yield: 1.31 g, 78%). The crude product was then dissolved in a minimum volume of CH2Cl2, then loaded onto a 40 g Isco RediSep normal phase silica cartridge, and purified on an Isco OptiX10 CombiFlash instrument using a gradient that started at 100% methylene chloride and ended at 90% methylene chloride, 9% methanol, 1% concentrated ammonium hydroxide. Fractions containing desired product were pooled and concentrated under reduced pressure. Yield of 42: 1.01 g (60% over two steps). 1H NMR (400 MHz, DMSO-d6) δ 2.21 (s, 6H), 2.49 (m, 2H), 2.58 (s, 3H), 4.77 (m, 1H), 5.40 (bs, 1H), 6.86 (d, J=5.6 Hz, 1H), 7.16 (dd, J=7.2, 1.6 Hz, 1H), 7.29 (t, J=8.8 Hz, 2H), 7.64 (m, 3H), 8.45 (d, J=5.6 Hz, 1H), 9.32 (d, J=7.2 Hz, 1H). MS (ESI+) 424.2.

Workup

  1. customThe reaction was then quenched with 16 mL of a 20% NH4Cl aqueous solution
  2. concentrationconcentrated under reduced pressure
  3. additiondiluted with water
  4. extractionThe solution was then extracted with methylene chloride (3×50 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a94a29055fb04529b500a0bdbee6977b
Source dataset
uspto-grants-2009_03
Patent number
US07504501B2

Reaction notes

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