Hydrochloric Acid → HCID 9947844, compound

HRID 1953821Notes

Reaction equation

HRID 1953821 reaction equation
[C:1]([C:3]1([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)[CH:9]=2)[CH2:6][C:5](=[O:7])[CH2:4]1)#[N:2].[BH4-].[Li+].[Cl-].[NH4+].Cl>O1CCCC1.O>[C:1]([C:3]1([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)[CH:9]=2)[CH2:6][CH:5]([OH:7])[CH2:4]1)#[N:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 4148881Lithium borohydrideHCID 9838782HCID 9838782, compound

Product 1

HCID 9947844HCID 9947844, compoundYield 102.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-cyano-3-(3-cyclopentyloxy-4-methoxyphenyl)cyclobutan-1-one (8.63 g, 30.3 mmol) in tetrahydrofuran (200 mL) at -78° C. under an argon atmosphere was added over 75 min a slurry of lithium borohydride (1.98 g, 90.8 mmol) in tetrahydrofuran (200 mL). The reaction was stirred for 0.5 h, and was carefully poured into a 0° C. saturated solution of ammonium chloride. 10% Hydrochloric acid was used to adjust to pH 3-4, the mixture was warmed to room temperature, was diluted with water and was extracted with three portions of tert butyl methyl ether. The organic extract was dried (magnesium sulfate) and evaporated to provide crude product (8.96 g, 100%) as a pale green oil. 1H-NMR shows an isomer ratio of ~3:1 cis: trans.

Workup

  1. extractionwas extracted with three portions of tert butyl methyl ether
  2. extractionThe organic extract
  3. dry with materialwas dried (magnesium sulfate)
  4. customevaporated

Sources & evidence

ORD record
ord-0854cbc335934aea8f01cecf50dd4ef3
Source dataset
uspto-grants-2000_09
Patent number
US06118017

Reaction notes

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