Ammonium Chloride → HCID 86692642, compound

HRID 1748691Notes

Reaction equation

HRID 1748691 reaction equation
[BH4-].[Li+].C([O:5][C:6]([C:8]1([C:18]2[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][N:19]=2)[CH2:17][CH2:16][C:11]2([O:15][CH2:14][CH2:13][O:12]2)[CH2:10][CH2:9]1)=O)C.[Cl-].[NH4+]>O1CCCC1>[Br:24][C:21]1[CH:22]=[CH:23][C:18]([C:8]2([CH2:6][OH:5])[CH2:17][CH2:16][C:11]3([O:15][CH2:14][CH2:13][O:12]3)[CH2:10][CH2:9]2)=[N:19][CH:20]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4148881Lithium borohydride2×HCID 86692455HCID 86692455, compound

Product 1

HCID 86692642HCID 86692642, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium borohydride (1.71 g) was added at room temperature to a solution of 8-(5-bromopyridin-2-yl)-1,4-dioxaspiro[4.5]decane-8-carboxylic acid ethyl ester (7.26 g) described in Reference Example 81(2) in tetrahydrofuran (100 ml) and stirred at the same temperature for 39 hours. Then, lithium borohydride (855 mg) was added and stirred at the same temperature for 24 hours. After completion of the reaction, a saturated aqueous solution of ammonium chloride was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated. The resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) to give [8-(5-bromopyridin-2-yl)-1,4-dioxaspiro[4.5]dec-8-yl]methanol (5.17 g) as a colorless transparent oil.

Workup

  1. stirringstirred at the same temperature for 24 hours
  2. customAfter completion of the reaction
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-137c258b7d224bfba3ab3da29538813b
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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