Water → HCID 69650328, compound

HRID 1789885Notes

Reaction equation

HRID 1789885 reaction equation
CC(C[AlH]CC(C)C)C.C([O:12][C:13](=O)[C:14]1[CH:19]=[C:18]([CH:20]=[CH2:21])[C:17]([N:22](C(OC(C)(C)C)=O)[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[N:16][CH:15]=1)C.[NH4+].[Cl-].O>C1COCC1>[C:26]([O:25][C:23](=[O:24])[NH:22][C:17]1[C:18]([CH:20]=[CH2:21])=[CH:19][C:14]([CH2:13][OH:12])=[CH:15][N:16]=1)([CH3:29])([CH3:27])[CH3:28]

Participants

6

Reactant 4

HCID 962WaterHCID 14487Diisobutylaluminum hydrideHCID 25517Ammonium ChlorideHCID 53818813HCID 53818813, compound

Product 1

HCID 69650328HCID 69650328, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

DIBAL (25 ml, 1M in hexane) was added dropwise to a solution of 6-bis(tert-butoxycarbonyl)amino-5-vinyl-nicotinic acid ethyl ester (2.00 g, 5.1 mmol) in THF (40 ml) at 0° C. The mixture was stirred at room temperature for 1 h. NH4Cl (sat.) was added carefully followed by water, and the mixture was concentrated under reduced pressure. The residue was suspended in 5% MeOH in dichloromethane and filtered through silicagel. The filtrate was dried and concentrated under reduced pressure to give (5-hydroxymethyl-3-vinyl-pyridin-2-yl)carbamic acid tert-butyl ester (1.00 g, 78%).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. filtrationfiltered through silicagel
  3. customThe filtrate was dried
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5cb79addc89149d0942dd732ab1be80b
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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