Sodium borohydride → 7-(Hydroxymethyl)-4-azaspiro[2.4]heptan-5-one

HRID 595261Notes

Reaction equation

HRID 595261 reaction equation
[BH4-].[Na+].[O:3]=[C:4]1[CH2:10][CH:9]([CH:11]=[O:12])[C:6]2([CH2:8][CH2:7]2)[NH:5]1>CO.O>[OH:12][CH2:11][CH:9]1[C:6]2([CH2:8][CH2:7]2)[NH:5][C:4](=[O:3])[CH2:10]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 916185615-Oxo-4-azaspiro[2.4]heptane-7-carbaldehyde

Product 1

HCID 916184147-(Hydroxymethyl)-4-azaspiro[2.4]heptan-5-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Sodium borohydride (1.4 g, 6.6 mmol) was added to a stirred solution of 5-oxo-4-azaspiro[2.4]heptane-7-carbaldehyde (0.51 g, 3.3 mmol) in methanol (8 mL) and water (12 mL) at 0° C. The reaction mixture was allowed to warm to room temperature and stirred for 1 hour. The reaction mixture was dried over sodium sulfate and concentrated under reduced pressure to afford the crude product residue. The crude product residue was purified by silica gel chromatography (1:10 methanol in dichloromethane, Rf=0.4) to give 7-(hydroxymethyl)-4-azaspiro[2.4]heptan-5-one. 1H NMR (400 MHz, CD3OD) δ 3.65-3.42 (m, 2H), 2.73-2.55 (m, 1H), 2.46-2.22 (m, 2H), 1.11-0.92 (m, 1H), 0.83-0.59 (m, 3H).

Workup

  1. dry with materialThe reaction mixture was dried over sodium sulfate
  2. concentrationconcentrated under reduced pressure
  3. customto afford the crude product residue
  4. customThe crude product residue was purified by silica gel chromatography (1:10 methanol in dichloromethane, Rf=0.4)

Sources & evidence

ORD record
ord-a153221c65cc478a8b9605a10055c552
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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