Phosphate → Cyclopropyl(phenyl)methanol

HRID 1770069Notes

Reaction equation

HRID 1770069 reaction equation
C1N=C(N)C2N=CN([C@@H]3O[C@H](COP(OP(OC[C@H]4O[C@@H](N5C=C(C(N)=O)CC=C5)[C@H](O)[C@@H]4O)(O)=O)(O)=O)[C@@H](O)[C@H]3O)C=2N=1.[CH:45]1([C:48]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)=[O:49])[CH2:47][CH2:46]1.P([O-])([O-])([O-])=O.[OH-].[Na+]>C(OCC)C.CCCCCC.CC(O)C>[C:50]1([CH:48]([CH:45]2[CH2:46][CH2:47]2)[OH:49])[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1

Participants

8

Reactant 4

HCID 1061PhosphateHCID 14798Sodium HydroxideHCID 77029Cyclopropyl phenyl ketoneHCID 439153Nadh

Product 1

HCID 66090Cyclopropyl(phenyl)methanol

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolventHCID 8058HexaneSolvent2×

Procedure

A reaction mixture was formed by admixing (i) 50 mg NAD, (ii) 4 ml of 2-propanol and (iii) 5 mmoles of phenyl cyclopropyl ketone, Compound 7, in a liquid medium containing 1 gm of lyophilized PED alcohol dehydrogenase preparation, 75 ml of 50 mM phosphate buffer, pH 7.1, and 25 ml of hexane. The pH value of the reaction was maintained constant by addition of 1N NaOH. The reaction mixture was maintained at room temperature until product formation stopped. When product formation stopped, phenylcyclopropyl methanol, Compound 7a, was isolated by removal of the hexane layer and extraction of the aqueous layer with ethyl ether (3×75 ml).

Workup

  1. customA reaction mixture was formed
  2. additionin a liquid medium containing

Sources & evidence

ORD record
ord-954bdff72c2c4f788975f9aeca8771ca
Source dataset
uspto-grants-1995_01
Patent number
US05385833

Reaction notes

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