Water → 1'-Benzyl-6-bromo-4-hydroxy-spiro[chromane-2,4'-piperidine]

HRID 2046698Notes

Reaction equation

HRID 2046698 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([CH2:22][C:21](=[O:23])[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([Br:24])[CH:19]=3)[O:14]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].O>CO>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([CH2:22][CH:21]([OH:23])[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([Br:24])[CH:19]=3)[O:14]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 128879551'-Benzyl-6-bromospiro[chroman-2,4'-piperidin]-4-one

Product 1

HCID 529521961'-Benzyl-6-bromo-4-hydroxy-spiro[chromane-2,4'-piperidine]Yield 99.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1′-benzyl-6-bromo-spiro[chromane-2,4′-piperidine]-4-one (3.0 g, 7.8 mmol) and NaBH4 (1.47 g, 38.75 mmol) in MeOH (20 ml) was stirred at RT. After 3 h, the solution was poured into water and the product was extracted with DCM (50 ml). The organic phase was dried over Na2SO4, filtered and evaporated under vacuum to give 1′-benzyl-6-bromo-4-hydroxy-spiro[chromane-2,4′-piperidine] (3.0 g) as a light yellow solid.

Workup

  1. extractionthe product was extracted with DCM (50 ml)
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated under vacuum

Sources & evidence

ORD record
ord-d234f0477d2d4badb21ecf39c75919eb
Source dataset
uspto-grants-2013_11
Patent number
US08592444B2

Reaction notes

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