Sodium borohydride → 3,4-Dihydroxy-2-(3-hydroxyoctyl)cyclopentane carbonitrile

HRID 1580783Notes

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

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 pg,42 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 3,4-di(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-da2d4aceef99425bad71a1c5b9cdff1a
Source dataset: uspto-grants-1976_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03933890

Reaction notes

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