Phosphate → [(1S,2S)-2-phenylcyclopropyl]methanol

HRID 1770068Notes

Reaction equation

HRID 1770068 reaction equation
C1N=C(N)C2N=CN([C@@H]3O[C@H](COP(OP(OC[C@H]4O[C@@H](N5[CH:36]=[C:35]([C:37](N)=[O:38])[CH2:34][CH:33]=[CH:32]5)[C@H](O)[C@@H]4O)(O)=O)(O)=O)[C@@H](O)[C@H]3O)C=2N=1.[C:45]([C:53](OC)=O)(=O)[C:46]1C=CC=C[CH:47]=1.P([O-])([O-])([O-])=O.[OH-].[Na+]>C(OCC)C.CCCCCC.CC(O)C>[C:33]1([C@H:34]2[CH2:36][C@@H:35]2[CH2:37][OH:38])[CH:32]=[CH:47][CH:46]=[CH:45][CH:53]=1

Participants

8

Reactant 4

HCID 1061PhosphateHCID 14798Sodium HydroxideHCID 84835Methyl phenylglyoxalateHCID 439153Nadh

Product 1

HCID 6427564[(1S,2S)-2-phenylcyclopropyl]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 1-carboxyaldehyde-2-phenylcyclopropane (Example 5), Compound 5, 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 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, (S,S)-2-phenylcyclo-propylmethanol, Compound 5a, 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-88be013a3b954863836d77ef8bae92e8
Source dataset
uspto-grants-1995_01
Patent number
US05385833

Reaction notes

Loading…