Sodium borohydride → 3,4-Dihydroxy-2-(3-hydroxyoctyl)cyclopentane carbonitrile
Reaction equation
C([O:4][CH:5]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:6][CH2:7][CH:8]1[CH:12]([C:13]#[N:14])[CH2:11][CH:10]([OH:15])[C:9]1=[O:16])(=O)C.[BH4-].[Na+]>CO.[OH-].[Na+]>[OH:16][CH:9]1[CH:10]([OH:15])[CH2:11][CH:12]([C:13]#[N:14])[CH:8]1[CH2:7][CH2:6][CH:5]([OH:4])[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
A stirred solution of 2-(3-acetoxyoctyl)-3-cyano-5-hydroxycyclopentanone (23.5 g.) [prepared as described in (j) above] in methanol (135 ml.) was treated dropwise, during 15 minutes, with a solution of sodium borohydride (13.2 g.) in 0.2N aqueous sodium hydroxide solution (70 ml.) at 15°-20° C. After 1 hour the solution was slowly heated to 50° C., stirred at 50° C. for 3 hours, and then allowed to stand at room temperature overnight. Methanol was removed in vacuo, water (75 ml.) was added and the mixture acidified by means of concentrated hydrochloric acid. The mixture was extracted with diethyl ether and the ethereal extract was washed with water, dried with magnesium sulphate and evaporated in vacuo to give crude 3,4-dihydroxy-2-(3-hydroxyoctyl)cyclopentane carbonitrile (16 g.), which was used in the following preparation (1) of 3,4di(2-tetrahydropyranyloxy)-2-[3-(2-tetrahydropyranyloxy)octyl]cyclopentane carbonitrile without further purification.
Workup
- waitto stand at room temperature overnight
- customMethanol was removed in vacuo, water (75 ml.)
- additionwas added
- extractionThe mixture was extracted with diethyl ether
- extractionthe ethereal extract
- washwas washed with water
- dry with materialdried with magnesium sulphate
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-cd53ed672cac4c039361e5d6d9b4bd54
- Source dataset
- uspto-grants-1978_05
- Patent number
- US04088821
Reaction notes
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