Borane;tetrahydrofuran → HCID 10132115, compound

HRID 1351574Notes

Reaction equation

HRID 1351574 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17](=O)[NH:18][C:19]2[CH:24]=[CH:23][N:22]=[CH:21][C:20]=2[OH:25])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B.C1COCC1>>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]([CH2:17][NH:18][C:19]2[CH:24]=[CH:23][N:22]=[CH:21][C:20]=2[OH:25])[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 69415271HCID 69415271, compound

Product 1

HCID 10132115HCID 10132115, compound

Procedure

EXAMPLE 106 was prepared from 4-(3-hydroxy-pyridin-4-ylcarbamoyl)-piperidine-1-carboxylic acid benzyl ester (which was prepared by EDC coupling of 4-amino-pyridin-3-ol and N-benzyloxycarbonyl piperidine-4-carboxylic acid) by borane-THF reduction overnight at room temperature. The reaction was quenched by slow addition of 1N HCl until pH=2, then basified to pH=10 with 10N NaOH. Extraction with chloroform yielded a crude product which was purified by preparative chromatography, eluting with 90:10 chloroform saturated with ammonia: methanol to give 4-[(3-hydroxy-pyridin-4-ylamino)-methyl]-piperidine-1-carboxylic acid benzyl ester: MS (m+1)=342.4.

Workup

  1. customThe reaction was quenched by slow addition of 1N HCl until pH=2
  2. extractionExtraction with chloroform
  3. customyielded a crude product which
  4. customwas purified by preparative chromatography
  5. washeluting with 90:10 chloroform saturated with ammonia

Sources & evidence

ORD record
ord-04c68c09f6d54e5a9b7f93664b24a29f
Source dataset
uspto-grants-2007_05
Patent number
US07217716B2

Reaction notes

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