Sodium borohydride → HCID 44253508, compound

HRID 518177Notes

Reaction equation

HRID 518177 reaction equation
Cl.[CH2:2]([N:9]1[CH2:14][CH2:13][C:12]2([CH2:23][C:22](=[O:24])[C:21]3[C:16](=[CH:17][CH:18]=[C:19](/[CH:25]=[CH:26]/[C:27]([NH:29][OH:30])=[O:28])[CH:20]=3)[O:15]2)[CH2:11][CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[BH4-].[Na+]>CO>[CH2:2]([N:9]1[CH2:14][CH2:13][C:12]2([CH2:23][CH:22]([OH:24])[C:21]3[C:16](=[CH:17][CH:18]=[C:19](/[CH:25]=[CH:26]/[C:27]([NH:29][OH:30])=[O:28])[CH:20]=3)[O:15]2)[CH2:11][CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 52951036HCID 52951036, compound

Product 1

HCID 44253508HCID 44253508, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (E)-3-{1′-benzyl-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-N-hydroxy-acrylamide hydrochloride (60 mg, 0.14 mmol) and NaBH4 (17.6 mg, 0.459 mmol) in MeOH (5 ml) was stirred at RT. After 3 h, the solution was evaporated under vacuum. The crude residue was purified by preparative HPLC to give (E)-3-{1′-benzyl-4-hydroxy-spiro[chromane-2,4′-piperidine]-6-yl}-N-hydroxy-acrylamide (45 mg) as its trifluoro acetate salt.

Workup

  1. customthe solution was evaporated under vacuum
  2. customThe crude residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-e09c2e73d62f4f449844045dd865e851
Source dataset
uspto-grants-2015_08
Patent number
US09115148B2

Reaction notes

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