Sodium borohydride → HCID 23346464, compound

HRID 1856278Notes

Reaction equation

HRID 1856278 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]2([CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:6]=1)=[O:4].[BH4-].[Na+]>C(O)C.O>[Br:1][CH2:2][CH:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]2([CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:6]=1)[OH:4]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 23346443HCID 23346443, compound

Product 1

HCID 23346464HCID 23346464, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

3'-Bromoacetylspiro(cyclopentane-1,1'-indene) (7.5 g) in ethanol (150 ml) is stirred at about 20° C. with sodium borohydride (3.0 g) for 15 minutes. The solution is diluted with water and extracted three times with diethyl ether. The extracts are dried and the solvent removed, giving crude 2-bromo-1-[spiro(cyclopentane-1,1'-indene)-3'-yl]ethanol. This bromohydrine is dissolved in dioxane (75 ml) and dimethylamine (10 g) is added. The solution is heated in an autoclave at 90° C. for 2 hours. Evaporation of excess of dimethylamine and solvent gives an oily residue, which is treated with 2 N sodium hydroxide solution. Extraction with dichloromethane, drying of the extract and evaporation of the solvent gives the title amine as a colourless oil, which on treatment with oxalic acid in acetonitrile solution is converted to the crystalline hydrogen oxalate; m.p. 133°-134° C. after crystallization from acetonitrile.

Workup

  1. extractionextracted three times with diethyl ether
  2. customThe extracts are dried
  3. customthe solvent removed

Sources & evidence

ORD record
ord-490872dc1e98438797309b33f497ba0e
Source dataset
uspto-grants-1980_08
Patent number
US04218472

Reaction notes

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